My Life as Savannah Chapter 1 – My Early Years

This story is not like other stories that I’ve read, saying “I’ve always known I was a girl”. I think I discovered I wanted to be a girl.

The Thomas family lives just on the outskirts of a small rural town that has a population of approximately 4,000. Our town lies about an hour or so East of Atlanta and an hour south of the Chattanooga National Forest were the Blue Ridge Mountains are located. Historically, there were many Civil War battles in our region. I am a seventh-generation child. My family consists of my Mother (Karen Taylor), Father (Kenneth Robert), Gwen Lee (my older Sister), and me, Kenneth Robert II. Father’s side has a lineage documented back to the Sons of the American Revolution.

During my formative years, like many young boys, I would occasionally sneak in the bedrooms of my Mother and older Sister and try on their bras, panties, and slips. I loved the smooth feel of the silk, satin, and lace against my skin, and I pretended to have breasts and often dreamed what it would feel like to have them. This was about the extent of my explorative dressing. Most of the time, I was a genuine tomboy and did all the usual boy stuff – baseball, swimming, fishing, etc. I never wore girl clothes out of the house.

Around the age of nine, things changed. I began to notice some of the older girl’s breasts developing and long legs, and observed more bras and bra straps through blouses and tops. This enticed me even more and caused me to wear my Mother’s and Sister’s clothes more. Occasionally, I would wear my Sister’s panties outside under my male drab. This excited me. I wasn’t very sexual yet but had a couple of exploratory encounters with my buddies. I had no idea what a transgender person was being raised in the deep religious Baptist South.

I loved going to our church mixers and the feel of girls’ skirts as they swayed over my legs, along with the feeling of their bras with my hand on their back when we slow danced. Plus, how they walked, smelled from their shampoo’s, body lotions, and perfumes, and added to that, the softness of their hands and smoothness of their skin simply mesmerized me. This, I think, is when I discovered I wanted to be just like them.

On Thursday morning in mid-April, during spring break, my Sister, Gwen, caught me, again, red-handed in her underwear drawer.

“What do you think you are doing, Kenny? And why are you in even in my room again?” I did not have any legitimate answer for her, or for that matter, one that would satisfy her. She caught me so many times, and I kept promising her I’d never do it again, but I did and kept getting caught. I’d begged and promised that I’d do anything to keep her from telling Mom and Dad. This time being caught one too many times finally exhausted my Sister’s patience.

“Okay, Kenny, you seem to like girls’ clothes let’s get you dressed as one.”

Gwen made me undress then commenced dressing me up in some of her old clothes; I pretended to object. Everything didn’t fit since I was smaller than her, and she was almost two-plus years older than me. Wearing her bra, panties, coupled with all the silk and satin and light makeup and lipstick, put goosebumps all over me, causing an erection. Gwen allowed me to wear her panties for the rest of the day. But first, she showed me how to hand wash them. Deep in my gut, I felt Mother might have known or Sis told her, but I could never prove it.

I have a small frame. 5”1” 74.3 lbs. No one else in my family or relatives that I knew of was this small. In school, I was too small for most sports. And too scrawny for contact sports like football. too short for basketball and volleyball, but I did very well academically. And because of not being in sports I had few real friends because most of the other boys played sports, so I kept to myself a lot.

Our father traveled extensively. When he was home, he and Mother would take a couple of weekend trips away together and Gwen would babysit me. Gwen would dress me and take me out to our backyard, where we’d play card games on the patio table. Our backyard is surrounded by a tall wooden fenced that surrounds our back yard and has honeysuckle vines entangled all over it. Although I was safe from anyone seeing me, I was still worried and kept looking around. On several occasions in the evenings, just after dark, she would take me for a walk around our neighborhood with her. The cool evening spring breeze felt cold up under my skirt after sitting with my legs crossed for a long time. Our neighbors would call and wave to us, so I tried to stay on the opposite side of Gwen so that I wouldn’t be recognized. One time, a few older boy’s driving down the street would honk their car horns or whistle cat calls out their window at us. Although not wanting to be recognized, I loved the attention of the boys thinking I was a girl.

Sis would also dress me and make me walk several blocks by myself and drop a letter in the mailbox. Although scared to go out without my Sister, I always seemed to manage to come back home unscathed and unrecognized. This morning she sent me out to get yesterday afternoon’s mail that was in our curbside mailbox when the paperboy came by. His name is Larry Morrison. I knew him from school and church. He said hello and handle me the newspaper and said, hello. When he left, I quickly ran back into the house, frightened to death.

“You did just fine. But girls don’t run like that.” Sis exclaimed.

Gwen seemed to love dressing me more and more when Mom and Dad were away. Sis took me almost everywhere she went. I appreciated her not embarrassing me. Soon I really couldn’t wait for Mom and Dad to leave so Sis could dress me up and show me all kinds of girl stuff. By this time, Gwen would tell me to go upstairs and get myself dressed, and she would show me more makeup, hair tricks, and mannerisms.

Gwen was having fun with me, and I was thoroughly enjoying it.

I was happy being dressed by Sis, and even more thrilled, I never caught my Mom or Dad.

Next: Mother finds out.

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Tags: crossdressing, featured, fiction, Transgender

Category: Fiction