I was about 4 or 5 when I had my first thoughts about dressing up like a girl. I remember having a wonderful dream in which I was in a dress and my hair was long. This dream was so powerful that I asked my mother the next day if I could actually do it. She told me yes but this never materialized into anything.
So, how about all of you out there? If you’re a crossdresser, do you remember your first memory of it?
JessicaWhoHD
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{ 3 comments… read them below or add one }
Hi Jessica,
Yes like you, I too was about 4 or 5 years old at the time (pre school going age anyway) and I remember sitting on my mother’s huge double bed and watching my Mom dress. First watching her remove her nightie and then, very carefully put on her clean panties, matching bra and suspender belt (these were the late 1950′s and ladies fashion was very feminine indeed) and then very gingerly put on her gorgeous nylon stockings. Next she would select the dress and appropriate high-heeled shoes and put them on before applying her make-up and finishing off with brushing her thick, curly gark brown hair. Then with her beautifully manicured and painted finger nails just perfect, she would be ready for the day. It was probably that very first time that I witnessed this daily ritual, that I knew that I wanted to grow up exactly like her and wear all the feminine things that she wore and it wasn’t long before I started “borrowing” her lingerie and ultimately all her clothes and make-up. She never really encouraged my interest in experiencing femininity, but she never actually discouraged it either and thinking back on those wonderful mornings and days, I believe that she might well have left items of clothing and make-up “lying” around in her room deliberately. But …… who knows??
I took full advantage of it anyway and she never ever mentioned it to me so I have always assumed that it was (and always has been) my secret alone. Only recently did I make the mistake of sharing it with anyone. My wife. ……. But that’s another disastrous story.
Thanks for your wonderful website and I must just say that as a blonde you look simply stunning.
Hugs and kisses.
Christine.
XXXXX.
When I was 15 the summer between grades 9-10th. For some reason few weeks before this feeling came over me. I just wanted to dress like a girl. So my mom had this one piece bikini that was purple with flowers on it. I said to myself ok today I am going to put it on for 10 mints and this feeling will go away and it did for that day. The next few days the feeling came back and once again I put on the bikini and kept it on for 2-3 hours and woundn’t you know it years later. This past summer I for the first time walked outside out my door and around my house as a crossdresser.
Like Jessica, i too started young. i was 5 when i remember i took a few pair of pannies from a cousin, then threw away my own for good measure. later my parents got divorced and i was at my dad’s gf’s house. she had a teen daughter who was rather pretty. one day, as punishment for hiding in her mom’s room while her mom was dressing, she dressed me up in her small clothes and i even got to pick what i was to wear. she made up stories that when i am in pulic or school i wished to dress like a girl and sit, walk, and talk in a chic way and live as a girl. i think she should be a Seer, because the feeling i had when i was 5 grew stronger and it was the best punishment ever because i felt good inside. now, i am turning 18 and my mom has found my clothes many times and is angry at me; i have worn her clothes. i am turning 18 soon and my parents are not supportive. they hope i shall stop. she says i can crossdress, but under her roof. and she doesnt differentiate between homosexual and crossdressing .i hope this wont be a disaster.