I can remember being 5, because i was in kindergarden, and putting on my sisters panties instrad of mine. I had a babysitter that use to dress me as a girl in order to punish me for being bad. Needless to say I was a horror to her.
I can remember being 5, because i was in kindergarden, and putting on my sisters panties instrad of mine. I had a babysitter that use to dress me as a girl in order to punish me for being bad. Needless to say I was a horror to her.
I was between 3 and 5 years old not sure exactly how old but I have a very clear picture in my mind of my mom and my aunt trying on clothes at my grandparents house. They were walking around the house in their panties and bras. It is one of my earliest memories and soon after I tried on my mom's panties for the first time. I was definitely caught at least once and scolded but nothing really happened. I continued to be fascinated with her underwear for several years....after my parents divorce when I was almost six my mom remarried within a year and we moved. She had this NFL football throw pillow that she was making me and she stuffed it with her old panties and slips. Of course I found this and used the items to dress up in at every turn. I also used to wear her panties, bras and slips when she was out..this was all before junior high school. I was pretty advanced for a pre teen kid. I was always envious when we would go shopping and go through the lingerie dept. I wanted those pretty panties and lingerie in the worst way but couldn't let on. I also used to borrow my step mothers panties when I would stay at their house. She had the sexiest panties I had ever seen. This went on for a while until she busted me wearing them under my robe, I was 14! She then discovered all her missing panties in between my mattress. I was sooooo embarrassed. We all had a little talk about privacy etc...and I promised never to do it again. They chalked it up to teenage hormones...but I just really loved wearing her panties. Finally into high school I was able to mail order panties to my house discreetly because I was home alone usually when the mail arrived. I also had a GF in high school that let me wear lingerie when we did "stuff". Once I got caught and just said that the panties belonged to my GF. Whew!
I think I started at about 10 or so.Well it's been better then 50 years now.
Angie
About 11 years old i had urges before and was able to resist for a while .One night i was whatching Happy Days no one was home i went to my mom;s closet and tried on one of her dressess it has not stopped since
I have a hubcap diamond star halo
I started dressing at age 13 in Mother's and Grandmother's underwear and dresses. They went out shopping every Saturday leaving me alone in the house. I would raid the washing basket looking for femme clothes to try on. I especially loved Grandmother's longline brassieres and corsetry. Once i had put on stockings I was addicted. Xxx
When i was young i always dressedd in some heels and nylons than later bought flats and while was alone at home just enjoyed walking around the house!
I can remember when I was about 8 yrs old & trying on a girls swimsuit. I was a crossdresser ever since...
I don't have any crossdressing memories as a child. I know that I wanted to dress in female attire ever since I can remember. I guess I started trying on my mon's shoes when I was in junior high school and started dressing in closet in high school. This opened a new world for me. I have been hooked ever since.
Twirling almost every full skirt I wore when I was 11 or 12. I still like to twirl my skirts nowadays, but the effect is less obvious on my skirts now - they aren't as full as those I wore a decade ago.
I remember when I was about 5 or 6 putting on some of my moms old dresses and wishing that I was a girl
Too many childhood crossdressing memories to list.
Was enjoyable growing up.
One of many reasons to continue full on crossdressing as an adult.
I have three distinct incidents in my memory from age four, my earliest memories, none of them CD related. I went to live for a year with my grandparents the week after my fifth birthday, so I can date things pretty well at that age. I have many memories from that year, including my first CD questions after I met the twin sister of a friend. She was dressed in all the frills that mothers in mid-America dressed their little daughters back in 1960. I remember asking myself why I could not look like that. I asked my grandmother and my aunt, but I do not remember their response. Knowing them well, I can easily and accurately guess what they said, though.
My first dressing experience was age nine, a Halloween parade. Yes, I dressed in public before I dressed in private. That is probably why my parents set an age limit of ten for trick or treating: after two consecutive halloweens of my dressing as a female, they probably wanted to stop it. It did not stop. It merely went underground and started occurring year round.
Last edited by abby054; 04-22-2016 at 07:42 AM.
Somewhere between 5 and 10 I discovered my mother's slips. That was all I wore for a few years.
The memory is quite vivid except the age which is approximate but close. I was probably around 3 1/2 or so to my best estimation. But I clearly remember wearing an emerald green dress. It had a thin white piping around a collar. The front was vertically pleated, buttoned in the back and also tied in the back with a big bow. I remember the scratchiness of the slip producing the poofiness of the skirt, the shininess of the black shoes, the lacy ruffles around the socks and the bow clipped to my hair. I remember standing on our dining room table and looking into a very large mirror on the wall above a buffet and people telling me how pretty I was. After that I remember a yellow dress, a black red and white plaid dress. I remember being in a store with 3 angled mirrors and trying on dresses as I looked in that mirror again probably around 4 or so and at least once riding the bus home wearing a dress that was bought at the store (don't know if it was paid for?). I dressed as I pleased at home, played boy things but also had tea parties and played with dolls dressed as a girl. Then at age 5 I remember my kindergarten teacher scolding me for wearing a dress from a trunk filled with clothes for "dress up" play in the class. There was a little kitchen and I thought I could be the Mom. I was firmly told (scolded) by the teacher that as a boy, I shouldn't dress up as a girl....it was wrong. She called my parents into school and I got the lecture that boys wear pants and girls wear dresses even though prior to that time, there was acceptance. Maybe time to become a boy for once and all. So for nearly 60 years I dressed in secret, held that secret tight, lived with shame remembering my kindergarten teacher's scolding until 6 years ago. Came clean to my accepting wife. Life is now beautiful, peaceful and enjoyable. Too bad, at this point in my life it is also much shorter.
My earliest memory was at 10 years old on Halloween night. I didn't have a costume, so my older sister and mother dressed me as a girl. I remember as I was going around collecting candy, boys were wolf whistling at me. It made me feel special and that I was missing out on something? Before that I enjoyed playing with my sisters house and dolls, over playing with my toys. I didn't dress then and when dad caught me playing with my sisters things, the roof nearly came off the house. I never enjoyed, as a kid doing boy things. Never played baseball or joined the Boy Scouts and when we went to someone's house and the girls were playing with their things. I cried because I was being left out.
Oh hell, I must have been like 3. I was old enough to walk around the house and not be constantly looked at from my parents at all moments. I was a pretty good kid, I knew what was bad and didnt do it. I had freedom. I remember one day, sitting on my moms bed while she was doing something in her room and when she opened her closet, some sort of white floral dress, it was silky but not actually silk. I was like, I need to wear it. I dunno why, I don't think there was any good reason. So when my parents had company, i scuttled away and put it on, draped in fabric. I waddled outta the room, all the adults laughed. The next few times I tried, i got in trouble. After that, I kept it a secret. Now, as an adult? Eh. Some people know i do it, but not my parents. I dont feel like having to deal with that bag of issues.
"Some people might suggest that I'm a closest-case Male to Female Crossdresser. I simply inform them that the doors to Narnia are open. Are you comfortable enough to take a trip through the armoire?"
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Way too many memories to list. Very fond memories starting about the age of five. No sisters so I dressed up in moms clothes whenever I could. I can describe her wardrobe in great detail. I was in heaven when I reached the age when she would leave me home alone. She would call and check in on me from work asking how I was doing and I remember replying "Fine" while in her dress or skirt and blouse. Mom had nice things and I explored all of it.
Of all the assorted bits of memories, the CD start point was possibly in pre-teen when I liked to venture out in the quiet, safe suburban night to the park. One night I thought it was scandalous that I was wearing a jean jacket, a white t-shirt and mom's bra stuffed with socks.
I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
My new maid's outfit is cute. Sure fits tight.
And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
Smile, Honey! You look fabulous!
I was in my early teens - 13 or 14 in the days of the miniskirt. So every now and then the girls in class would provide and discreet peek and like most young boys I was fascinated by what I saw. I had a sister a year younger and on occasion, she would leave her panties in the bathroom. Temptation took over and soon I put them on and you can imagine the rest. Well, it became more thrilling to try more and more items of lingerie and well, the rest is history. Here I am more than a few years later still enjoying the same things.
I completely identify with you and love Secretes in Silk! My sister would play dress up and I always wanted to play too. I was completely fascinated with lipstick and lingerie by the time I was 12 or so. Loved my mothers slips, girdles and peignoirs!Originally Posted by Suzy Parker
Every inch a lady!
The earliest memory i have is, when I was 6 or 7, and fantasizing about a classmates yellow dress. At the time I had no idea why I was so fixated on that dress, and it wasn't until my preteen years that i got very curious. Lots of time as a latchkey kid to explore in the afternoons after school, and was only caught once by my dad...(don't think he believed the excuse given, but was never spoken of again). Its funny, how you stick to certain things, I still have a great fondness for the classic maidenform type slips and girdles from those days. I guess old habits die hard..
My earliest memory of crossdressing, or more accurately of wanting to crossdress, was in my early teens. I already like heels and wanted to try some. One of my aunt had left a lot of her old heels at my grandmother house. Unfortunately, i have never found some time to try them on since the house was never empty. However, later, I knew (I saw pictures) that when I was 3 or 4, my older sister used to dress me up as a doll for fun. But I have no memory of it.
One of the earliest memories I have is putting on mom's bra. I had to be 4 or 5. When I was about 9, mom walked in on me it the bathroom wearing me sister panties.( white with little yellow dasies)
She just said take them off. only time i was ever officially caught.
I had the opportunity to dress as a girl in private and then out at Halloween. I talk about my experience here: http://www.crossdressers.com/forums/...ress-you/page3
Happy to chat with anyone about the experience!
Some boys just can't help acting like girls...
My pictures: http://www.flickr.com/photos/mayatoronto/
For Halloween in 5th grade I convinced my mother to allow me to dress as a girl - red lipstick, blond wig and a princess costume. I always dressed for Halloween after that and the dressing really took over in my teens. Of course it helped that so many New Wave bands and Boy George were crossdressing. In high school my friends and I would go to a gay bar in the city to dance. Drag shows were are BIG revelation to me and before too long I was going out dressed. My mother caught me so many times dressing or seeing boys that she just gave up and accepted it, before later embracing me for who I am.
Every inch a lady!
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