Where did you first crossdress ?

[RickS]

In my sisters room.
In the summer both parents were gone to work. So it was just her and I there.
She would dress me as her little sister and we would play all day that way.

[Laycee]

My bedroom. I would change in the dark and then just lay in my bed in my sister's clothes.

[ChrissyW]

The first time I got dressed up was at home. Parents were out and I put bathing suit and pantyhose on in bathroom with grapefruit and my breasts.

[Wendae]

The first time fully dressed, less make-up was right after my first tour in Vietnam. I was suffering from opthamalgic migrains and bad temper bouts. PTST? I had an overwhelming drive to get dressed. My wife wasn't too thrilled with the idea but allowed me to do my thing if I stayed in the bedroom and she didn't have to see me. There was no tv in there(except me )and it was lonely but, it was better then nothing. We had only been married 3 years at the time. Eventually this activity became a bone of contention and I purged my things. After that it's been catch-as-catch-can.

[Bernice]

When I was in sixth grade, my parents were divorced. My mother frequently went to evening social engagements, leaving me to watch after my 2-year-old brother, who would sleep pretty well. The big TV (19 inch B&W) was in the basement, and I would frequently go nude, because I enjoyed the feeling. My mother left her clothing scattered all over the house.

A classic pale green pleated woven cotton shirtdress hung on the downstairs bathroom door. One evening it was rather cold for total nudity, and so I tried on that dress. It fit perfectly, and felt so good. I began wearing it at every opportunity.

Hugs,

Bernice

[MelodyPerkins]

I had been punished for something, and sent to my room. While listening to the play of the other children outside, I comforted myself by wearing my sister's dress.

My fondest memories are of me curling my hair with a curling iron at age 9, after my mother had gone to work. With my hair longer and curled, and a little make-up applied, I skipped off to school.

[Shawna]

For me was my mom's room is when I first got and tried on my pantyhose. Then there was also my aunts house. As I would stay there and visit. I was in her bathroom and she had some dark tan pantyhose hanging over her shower rod. I pulled them down and tried them on. They felt so good going on over my legs. As I was standing there marveling at my hose legs. I forgot to unlock the bathroom door and my aunt walked in on me in hose. She just looked at me and asked why was I in her pantyhose. I couldn't really think of anything to say. All I could come up with in a shakey voice was I don't know they feel good. She smiled and said so you like to wear my hose huh. I put my head down and said yeah. She said ok well lets get u tucked in for bed. I started to take the hose off. She said no you can keep them on. So I followed my grandma into the room I was staying. She said wait here and went into her room and came back with a white nighty that was about knee legnth on me. She said here wear this when you sleep. I took my shirt off and put the nighty on and climbed into bed. She said ok no get some sleep. She tickled my hose foot which felt kind of good in a way. I layed in bed rubbing my hosed legs. Then decided to have a little j/o session before bed. When morning came I got up and changed real quick. Later my aunt came in and found the hose and nighty by the door. She picked them up and just as she was starting to go out she noticed that my cum stains were on them. I was a little embarressed about that. She just smiled and said well I will wash these up so you can wear them when ever you would like to ok. I said ok. After which she said it will be our little secret.

[PhylissH]

Like most of you the first think I wore was mos pantyhose,and loved the snug silky feel. I was about 11 or 12. For as long as I can remeber I have been interesred in girls/ womens clothes. The first ime I really got dressed was at a friends house when I spent the night and we were left home alone. I had always been eyeing his sisters things that would be hanging in the bathroom.
Well for what ever reason he dared me to put on some of his sisters clothes, I did not even hesitate. I went right to the bathrooom and put panties, pantyhose and a pullover dress, unfortunately her shoes where too small.
After that I couldn't wait to spend the the night with my friend as we got left home most of the time. I was hooked

[Alana]

I first dressed in the bedroom I shared with three brothers when I was about 11 or 12. I would feign illness to get out of school. Both Mom and Dad were working then, so I had several hours to try things on without fear of being caught. Most of the items came from the Goodwill collection bags stored in the basement. I especially remember a long-line strapless bra. Sometimes I would try on Mom's girdles or swimsuit, and some Avon lipstick samplers.

Alana

[Martina]

My first time dressing was trying on a pair of my cousins frilly tennis panties in her bedroom. But when I started to really experiment with crossdressing around 13/14 I was allowed to lock myself into my mothers bedroom to study without distraction from my siblings because my grades were so poor. It was during this period that I discovered my mothers enormous collection of lingerie. I will never forget the hard on I experienced when I looked into that seemingly bottomless chest of drawers with frilly things from the 60's and 70's. I think that that experience triggered off something in my developing brain that got hard wired and left me permanently as a CDer. The prettiest things were at the back and I would try on different panties and nighties. Fridays were my favourite days because my mother would spend the afternoon out shopping and my siblings would play outside. I would use this time to dress up and try on the frilliest clothes with little fear of been cought.

[Lily]

My sister was 20 years older then me. So when I was about 7 or 8 I use to sneak up to her old room after she moved out and try on the prom dress, bathing suits and panties and bras. I was real young when I started putting on her cloth under my own and going out. I've been doing the same thing ever since.

[Karen]

In my Mom's bedroom. I eventually would sneak a couple of pair of panties to my bedroom. Lipstick was something I wanted to try early
on but Mom worked all day and didn't leave lipstick around.

[Donnie]

I started when I was away from home in college. I had my own appartment, which provided a safe place to wear whatever I wanted, whenever I wanted.

[Erica S]

I started in my Mom's bedroom. I was attracted by her girdles and nylons. It went from there...

Erica

[Anouk]

For me the very first time as far as I remember was when I tried one of my sister's fantasy skirt on. I must have been about four years old. The real crossdressing started in my sister's room as I was about ten.