I Remember My First Crossdressing Experience Stories of Experiences (Page 9)

A friend of mine lived next door and had a drop dead gorgeous mom that I fantisized about for a long time. I was eight at the time. One day we were outside playing football and I had to use the bathroom. Instead of going home I went...

When I was about 7 or so, I tried on my mom's panties and then pantyhose. They were too big, but felt incredible, silky, soft, smooth. I do not know what made me do it, but once I tried, I was hooked, So, I have been crossdressing...

It is better that you have read my part1 & 2 before this story.

I am now 17 years of age and wearing silky knickers every day under my male clothes, I am hooked on lingerie for life I think, I just love the feeling next to the skin, I...

i was twelve and coming home from the school disco i noticed two ladies walking in front of me wearing tights i really wanted to wear some tights i went home and found a pair of my mums in the c;lothes basket in the bathroom and put...

When I was about 15 I went and stayed at my Aunt's house for a week one Summer, I had been wearing my Mother's big silky knickers most days from the age of 12 and loved the feeling next to my skin, I think my Mother knew but she never...

I couldn't have been much more than 7 or 8 when we lived in a house that had a basement toilet we would use when the need arised.This qwas back in the 60's when we had first got a washer and dryer set that wasn't a ringer type maching...

I was 12 and I hurried home from School, straight into the house, upstairs and off with School Uniform.
I then went to Mother's drawers and took out a pair of Pink Directoire Knickers or some call them bloomers, it was 1963.I slipped...

I was 15 the summer of 1950 when I was persuaded to perform a dare. It was embarrassing at first but it was fun at the same time. Several of my friends, all about 15 years old, met a neighbors house for a cook-out one evening. When I...

I was 6 when it happened. My sister and her friends ganged up on me and put makeup on me. Along with that they put me in panties and a maroon pleaded dress with puffy shoulders. I looked like Shrley Temple and I loved it. Then, when I...

I do not know the exact time.I had been dressed in girly clothes all my life. My sister, who was 12 years older than I,raised me.
She fed me, dressed me, groomed me and bath me. We always played with dolls, and I did whatever she...

I was about 10 and I was at home alone. I was quite board so was just walking around the house when I found some of my mums panties. I decided to try them on and they felt amazing, I ran into her bedroom and starting playing with her...

I was 12 and I was bored one day. My moms friend left a bag with some of her clothes in it I peeked in there was this nice sexy green thong well a g string I grabbed the bag and went into the bath room I slip into the g-string and I...

i remember the first time I wore panties.  I remember the first time I bought panties (and the first time I bought Hanes panties, and the first time I bought satin panties).  I remember my first skirt.  I remember the first time I...

I really don't remember my first crossdressing experience. I was around 10 and I do remember finding one of Mother's girdles and asking her if I could try it on. She chuckled, and said OK. I did try it on and love the way it made me...

I got started with crossdressing in my pre-teen years, age 12 to be exact, when I found a box clothing which my step-mom had boxed up for Goodwill. When I opened the box and saw some of my older step-sister's clothes on top, I...

my 13th year i used to sneak out at night wearing sexy lingerie and the house behind ours had a nice high fence and i would go back there and dance around and just have fun being outside. i thought old people lived there because i have...

We lived in Anaheim and grew up in an urban neighborhood. My older sister was in 3rd grade and she wanted to take me to school with her. I was 5 years old. it was a bring your sister" to school theme, so, my mom and her dressed me up...

I remember my first time as tho it were yesterday,and it happened to be a day which had a couple of firsts...I can't ever remember what made me notice or be fascinated before but at the age of about 9 I remember looking in our airing...

I was 7 in 1959 and my sister Patrica 8, we were very close, she was a total tomboy who was accepted by my friends as ' one of the boys' and often hung out with us. Patrica was due to make her first communion. My Mum, my Aunt Peggy and...

I rember my first time dressing like it was yesterday i was about 10 and a only child who lived with his aunt she was a strong beautiful woman she had a great life and only wanted the best for me she had left me alone one day for what...