Flash from the past

We went to a park to walk the dog and get some fresh air for a change. I meet an old friend there that we lived next door to each other for about 20 years. My wife asked why we don't still keep in touch since we were so close. He was telling some back in the days stories and he told my wife his best recollection was when our mothers would go shopping and I would watch him and we would raid my sisters pantyhose drewers and we would prance around the house wearing them. He looked at me and said "do old habits die hard". We didn't say nothing but just smirked at each other, I should have lifted my pant leg and showed him that I was wearing pantyhose but I didn't think it was appropriate.
When we got home my wife was surprised at how far back in my youth this was part of my life and asked where did it start and if I remember the first time I tried on something femine and what drew me to it. I told her I thought of it many time and the only thing I can remember was when I was sharing room with my sister. She would leave before me and she was a slob and I remember seeing a pair of pantyhose and slip on the floor one morning and I tried them on and went to town with them and that was it, "I was hooked"
Does anyone else remember the first time and first thing you tried on and what drew you to try it on?

That is a good one, Maria! For all you know he could be a member here? Lol

I remember my first time. I was 7 and my sister was just born. We had a sitter one night when my parents went out on the town. While she was taking care of the baby and my brother I snuck into my mothers large walk-in closet. And started trying on everything. Bras, girdles, stockings and most memorable was a pink babydoll nightie with matching ruffled panties! I would sneak in there every chance I got.

My first attraction was my mother's white nylon full slips. The apartment was not suppose to have a washing machine in it, but it did. No dryer. My mother hanged her slips to dry on either a wash line strung down the hallway to the bedrooms or from a drying rack hanging from the bathroom ceiling. The way the clothes line was hung in the hallway you had to duck under it. I discovered I love the feel of the nylon slips. At first al I would do is fondle the slips. After a while I got the nerve to take a slip down off the bathroom hanging rack and try it on. I was hooked on the feel of nylon. Later it extended to her nylon nightgowns. I know it was before puberty.

Hi Maria :hugs:, around age 4 or 5 walking in my mom's shoes, >Orchid**O:daydreaming:O**

My trigger was a bustier my mother kept in the closet in my room.

My favorites were my mother's slips and lipstick. The slips felt heavenly when I put them on. They triggered, ahem, a pleasant and strong response, to put it in G-rated terms. Lipstick did too. But it wasn't just the physical response. It was also a gloriously wonderful feeling that somehow this was right for me. It called up very deep emotions that helped me to understand better why I wanted to be a girl so much. The feelings of wanting to be a girl, that I was somehow actually a girl, preceded the trying on of girl clothes by a couple of years. But seeing myself in the mirror with a full slip on and lipstick completed and validated the deeper feelings.

I do not recall my age at the time but I couldn't have been more than 7 or 8. As many others I have no clue what the attraction was but I recall finding a discarded bra in a box where we used to store clothing to be used for rags. I had to try it on. It was in the rag bin so I hid it away and later raided my mothers panty drawer. I had these items to myself for a long period of time. As time wore on I would find other items to try such as stockings. Needless to say I was hooked.

For me, it was around age 9. I had felt like wanting to be a girl at times before that, with my earliest memory of it around age 4. One day I was home alone, with my mom at work and my brother gone for the day somewhere. I was in my mom's room just snooping around, not looking to dress. But, then I found a pair of pantyhose and felt strongly compelled to try them on. The feeling blew my mind. I was in absolute heaven, completely hooked.

Home alone about 12 years old , home alone , for some unknown reason tried on sisters dress , God , that got me started and just could not stop after that completely hooked as the saying goes

Ever since I can remember I have been attracted to women's clothing. I was in the attic one day and saw one of mother's older one piece bathing suits hanging up. I sneaked it out of the house and wore it whenever I was playing in the woods around our place. When I was around 7 or 8 i was staying with my aunt who had a daughter my age. One rainy day my cousin wanted to play dress up and of course I went along with it. My aunt thought I looked cute in a dress and asked if i wanted to stay dressed up and be here niece. I was in heave for the next two weeks. After that I was always the niece when I spent time at their house. When my cousin and I were around 12 my aunt took us shopping and bought us a matching dresses and also frilly panties, bra, garter belt, stockings and small heels. OMG I was in heaven. Those stockings felt soooo good on my legs.

I was about 7 or 8 and found my mums one piece swimsuit on top of the laundry basket, without any thought of, should I? I put it on and with a couple of grapefruits for boobs I went and said tto my mum "now I am like you", all she said was "yes now go and take it off"; I always remember that day, and think that that must have been the start of what was to come in my life. I am glad it was.

Like Gretchen my feelings of wanting to be a girl started when I was 8. It was not until I was 11-12 that I started with my mothers things, one in particular was a OBG and I loved it. That led me to try on everything else, bras, stockings, slips and even dresses. I was just so happy when I did all this and it reinforced me wanting to be a girl.

When I was about 8 or 9 I would often play with my younger sisters. Our next door neighbor (a very attractive 20 something) gave them some of her old clothes for dress up. A couple pair of high heels were among the donation. When I tried on the heels, they fit perfectly. I was very disappointed when I outgrew them.

I was fascinated by women's legs in nylons from an early age -- dancers, figure skaters, girls in 60's skirts and dresses. One time I found an old pair of my sister's pantyhose in her trash can. I was home alone, and did it all wrong, but I got them on and felt exhilarated! Eventually saved a pair of discards until eventually working up the nerve to buy my own. Still love the feeling.

Hi Maria, Mine was when I was about 14 years old, I saw a dress at a secondhand store. I purchased it with shaking hands and practically ran out of the store. I tried it on that night in front of the mirror, it had a side zipper, I had never seen one before. As I zipped it up it drew the dress in around me and fit me perfectly. I stared at myself in the mirror, I couldn't believe the girl there was me. I was hooked on cross-dressing from that point on. Thanks for the fun memories. Brenda