My Life as Ashli — The Early Years

Introduction

This story is not like other stories that I’ve read in which the author says that they’ve always known they were a girl — I think I discovered being one.

The Thomas family lives just on the outskirts of a small rural town of Madison, Georgia. It lies about an hour or so East of the 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 the seventh-generation child and my family consists of my Mother, Father, Gwen (my older sister) and me, Kenny.

My Story

During my early years, like many young boys I would occasionally sneak in their rooms and put on my Mother’s and older Sister’s 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 dreamed what it would feel like to have them. This was about the extent of my dressing. Most of the time I was a genuine tomboy and did all the boy stuff – baseball, swimming, fishing, etc. I never wore girl clothes out of the house.

Around the age of 10 or 11 things really changed. I noticed the girl’s breasts and long legs and obviously that caused hormonal reaction. I noticed more bras and breasts through blouses and tops. This caused me to wear my Mother’s and Sister’s clothes a little more often, and occasionally I would wear my Sister’s panties outside under my male drab. This really excited me. I wasn’t very sexual yet but had a couple exploratory encounters with my buddies. I didn’t know what a transgender person was being raised in the deep religious Baptist South.

Soon I started going to church mixers and dances. Wow! The feel of girls’ skirts as they swayed over my legs, the feel of their bras with my hand on their back when we slow danced. Plus, how they walked, smelled and the softness of their hands and smoothness of their skin simply mesmerized me. This, I think, is when I really discovered I wanted to be just like them.

One day my sister, Gwen, caught me, again, red-handed one morning in her underwear drawer. “What do you think you are doing, Kenny? And why are you in even in my room again?” I really did not have any legitimate answer for her, or one that would satisfy her. In fact, she caught so me many times and I kept promising her I’d never to 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. 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 commended 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 8 years older. Wearing her bra, panties, coupled with all the silk and satin and light makeup and lipstick put goosebumps all over me. Sometimes I’d get an erection that really didn’t impress my Sister at all. One time I ejaculated in her panties. Now I knew I was in real deep trouble with her this time. So she showed me how and made me hand wash them and all her other underwear for a month. I felt Mother may have known or Sis told her, but I could never prove it.

I have a small frame. 5”3” 84.3 lbs. No one else in my family or relatives was this small, that I knew of. In school I was too small for most sports. I had few real friends since I didn’t do well in most sports, so I kept to myself a lot. Although I did do very well academically.

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 took me out to our backyard dressed up. There was a high wooden fence that surrounded our back yard and we simply sat on the patio chairs. Although safe I was still worried and kept looking around. She would make me walk around our neighborhood with her. The cool evening summer breeze felt nice up under my skirt. Our neighbors would wave at us, so I tried to stay on the opposite side of Gwen, so I wouldn’t be seen. On occasion a few older boy’s driving down the street would honk their horns or give cat calls at us.

Sis would also dress me and make me walk a couple blocks by myself and drop a letter in the mailbox. Although scared to go out without my Sister, I seemed to always manage to come back home unscathed and unrecognized.

One early morning she sent me out to get yesterday afternoon’s mail and the paper boy came by. It was, Larry. I knew him from school and church. He said hello and handle me the newspaper and said, hello. I ran back into the house frightened when he left

“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 gone, Sis would dress me and took me everywhere she went, and I really appreciated her not embarrassing me. Soon I really couldn’t wait for Mom and Dad to be leave so Sis could dress me up and show me all kinds of girl stuff. By now Gwen would tell me to go upstairs and get myself dressed and she would show me makeup and some hair tricks.

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

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

Next: Mother finds out.

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