I started early when my mom put me in panties. From there it was never the same. Wore my sisters, neighbor girls, and any other things I could wear.
I started early when my mom put me in panties. From there it was never the same. Wore my sisters, neighbor girls, and any other things I could wear.
I couldn't dress full out back then but I started at about 10 years old.I didn't dress fully until after I was merried in 1968. and only out to my wife about 7 years now.I spend more time in girl mode then in guy mode now.I it wasn't for work I'd have something on 24/7.
Angie
There were 3 girls across the street who dressed me up when I was maybe 7 or 8. I loved it Their mother discovered us and made me go home. After that I used to put on my NaNas sexy bikini when she wasn't home. I remember playing a witch in the 5th grade play and acting like I didn't like it. My junior year in high school I was a cheerleader at the powder puff football game. Again I acted like I didnt like it when I was so happy inside. Finally I dressed up one Halloween several years ago. Now I go out almost every week! It was a long journey!
Suzanne
I didn't know that all little kids didn't wear dresses and have their hair braided in pigtails until I went to the first grade. I couldn't figure out how come I had to dress up like a boy to go to school. Talk about a life changing experience. Didn't get to wear a dress much after that until I was 12 and got to spend the summer as a girl, but that is another story in itself.
I didnt start until i was 11 but i remember being really jealous from about 7 that i couldnt wear a pretty dress and have my hair pretty. I am still jealous of all those gorgeous women out there, so i guess nothing has changed lol x
I didn't have access to outer clothes that fit me remotely well until I was in my teen years. But my mom used to put lipstick and nail polish on me back when I was as small as three or so, and by the time I was 12, I was wearing heels regularly and had my ears pierced. I would wear all this (occasionally, not all the time) to go shopping with Mom and to visit her friends, but I was always in boy mode at school and among my peers.
- Diane
As a young boy I had no inclination of wearing feminine clothing. I had no sisters or female cousins. The only girl I associated with played center field on our team. She was a terrible baseball player. A girl way ahead of the times. She wore jeans and a tee shirt just like the guys. She had a great throwing arm. I never thought she should be in a dress like all the other girls of the 1950's and early 1960's. I bet she went on to be a real sexy and successful woman because she had confidence in herself.
Me? The only time I can remember ever wearing some feminine was in response to my mother saying once too many times that I was supposed to be a girl since my brother was born earlier. She wanted the perfect family; one boy and one girl. I cried and put on her nightgown and said she did not love me because I was not a girl. She reassured that she loved me and I think she never made those comments after that. I also recall being in kindergarten and the teacher saying she liked my cowboy shirt. She called it a blouse which really upset me.
I may have around ten when I discovered I liked the feel of nylon, specifically her nylon slips.
earliest recollections were when I was 4 or 5. I don't know if it was the nasty cold snap or dirty laundry or what but I remember wearing my sisters long white flannel long sleeved high neck gown to bed for a period. Don't remember the whys or for how long, but I do remember seeing a Christmas morning film when my sis and I walk into the living room to see what "Santa" brought us. She was in her Barbie gown and I in the whilte flannel gown. Film is about 2 seconds long then suddenly I'm in a long blue robe...but every now and then you can see the gown pop out from under the robe and towards the end of the footage the collar is out. I've seen many a photo and film of sis and I in the backyard playing and I'm either in her old playsuits, her old shorts sets or other 'hand-me-downs'.
My next memory was when I was 10 and spent 3 weeks at my Aunts while my parents went on a extended anniverary trip. Very long story short - They went to New York and Canada for about a week and I stayed with my Aunt and 3 girl cousins. They (parents) were doing the trip with friends so they dropped me at my Aunts on that morning and it was that night that it was realized my suitcase was either still at home or still in the trunk. So, I wore my cousins clothes for 3 weeks. Mostly her shorts and tops to start with, but also her bikini's and towards the end her dresses etc as well (I didn't want to be left out when they dressed up for church or went out for dinner!).
Well, when Mom/Dad got home, my Aunt convinced them that I could say a while longer (especially since her house was over an hour from home) so I ended up there 3 weeks. When Mom came to pick me up finally she had a cow when she saw me. At first, she couldn't tell me from the rest of the girls playing in the yard. I had on a pink shorts set, my hair was in pig-tails and my fingernails were also painted pink. She made me change back into the clothes I had on when I got there before we left and took out the pig-tails (which still left my hair pretty wavy for a few days after), but she didn't take off the fingernail polish till that night before going to bed. That was when she saw the training bra and panties I had on as well. When she took those off me was when she saw the 3 weeks worth of bikini tan lines that were well set into my skin. I didn't get to see my Aunt again for several years after until when my GrandDad died. I have written a story about that and its on Big Closet.
A Halloween between the above events I pestered my Mom to the point she let me go trick-r-treating as a girl wearing one of my sisters mini-dresses. It was a maroon velvet number with a high mock turtleneck top and long sleeves - and it was VERY short. Had a matching panty cover short. She did my makeup and I painted my nails and for shoes wore a pair of calf-high boots. Got back from T-r-T and was to go to a friends party but Mom said she couldn't find anything to take my makeup off with so I'd just have to go as I was. THAT was fun! Got a few comments about my "costume" but after a while I was accepted just like any other person. Even more fun was the parents that didn't know me treated me just like one of the girls, as did the girls after several hours. When I got home that night (late) Mom magically found her makeup remover but it was a couple of days later that she "found" her polish remover. I think she was trying to embarrass me but it didn't work.
Thats just a few of the times...
I started about 3-4 years of age. Right when we moved into a new house. Then I don't have any recollections of doing it again until I was 10. But the funny part is I was not dressing in anything age appropriate but in full grown women's clothing, my mom's.
In that respect, I was wearing pantyhose probably long before most real girls even slip into a pair. Even though most had probably worn tights by that time. Every now and then I'd try to squeeze into my little sister's leotards, which became my favorite article of choice.
Looking back I am very creeped out by it. That is one thing I'd change if I did it over, I'd be more pro-active about obtaining my own stuff.
The first time I dressed up as a girl was when I was 10. Every weekend I would go to my Aunt's house and play with my cousin who was five years older than me. I had noticed that she had started wearing tights, I was so envious of her. I begged her to dress me up fully as a girl in her dress tights and makeup. She would not let me wear her tights but she did give me one of her dresses to wear and she made me up. She had her girlfriend with her as well who also assisted with the makeup, I felt so girly. I didn't dress up again until two years later when I was twelve. I was wanted so much to be a girl. It was frustrating seeing all the girls in my high school class wearing tights. At the time in 1972, girls of my age wore tights underneath their school socks, it seems like a curious fashion now but I so wanted to be a girl just like them and wear knee high socks with tights. One day in late 1972, I plucked up the courage to go routing around my Mother's tights drawer. I pulled out a pair and tried them on, I was surprised to see how well they fitted me. Only problem was I didn't know if any of my Mum's skirts would fit me so I wore my football shorts as hot pants. A few weeks later I wore another pair of tights along with one of my Mums skirts which actually fitted me. I was in heaven. Thereafter I would dress up as much as I could each weekend when my parents were out for the evening. My dressing sessions were a little bit short probably a mixture of guilt and fear of being caught. My frustrations of envying the girls in my class continued. I was teased by the other boys in my class because I was hopeless at sport and was gentle and sensitive. The boys used to call me girl, I pretended to be annoyed but secretly I liked it because I had quite a few crushes on some of the boys in my school. At that time I had an almighty crush on Donny Osmond. I use to listen to his records at home and would swoon at his pictures. One of the boys who teased me said that I probably fancied Donny. I had told anyone about my crushes on boys but I again I was secretly pleased when this lad teased me about him. I continued to dress up at home throughout my teens and into my twenties. When I was twenty one I finally plucked up the courage to buy my own tights, I was a little embarrassed at first. Ever since then I have been buying my own clothes, I have purged many times. However a few years back I accepted my dressing and have not purged for three years. I am slowly re-building my wardrobe. As for tights/pantyhose I have drawers full of them. I love them so much. Sorry to relate such a long story but I have had fun telling it.
One of my older sisters used to dress me up as a girl when I was around four, I don't remember it but do remember sneaking into their bedroom when I was six and taking their stockings. I wasn't left by myself until I was in my teens and when I was left I had about four hours every Thursday to indulge in cross-dressing in my sisters bedroom. One of my sisters moved out but the other one is the one that used to dressed me up and her clothes were the one I would use to dress as a woman. Our parents would take trips and leave us at home when that happen I would take the liberty of get my sisters matching bra, panty and full slip wearing them along with some pantyhose and some of her perfume. I would also use her makeup but when question about it I would deny it. This went on for a few years until I couldn't stand it anymore and had to tell her about it. The sh*t hit the fan so to speak and she banned me from going in there and if I did she would tell our parents what I was doing. She eventually moved out also and I found a employment where I was making a little money and buying some feminine attire while living at home. Our parents would still go on vacation I would call in sick a day or two and dress as a woman, my sister would come by to check on me and one evening she found me dressed as a woman. She started to leave but changed her mind and came back to see if I wanted to talk I did but when I said we could have a woman to woman talk she got mad and said we can never have a woman to woman talk and I said a woman to whatever then. That is when I found out that she had dressed me as a girl when I was four.
Been trying things on for as long as I can remember, but, started going out in public when I was about 15---and never stopped!
"And if you want some fun, sing Ob-Bla-Di-Bla-Da!"
I found out that I liked the way nylons and panties felt when I tried on my moms stuff when i was about 5 yrs old. I didn't have alot of time to myself I had two older brothers and no sisters. I would sneak into my mom's room and raid her panty draw and run to the bathroom and try them on for awhile. As I got older I would take some pantyhose and wear them under my pants. Not till my brothers were older and out of the house with their friends and my parents went to the store did I try on my mom's dresses and skirts. During my teens 14 to 18 I had the house to myself alot and would try on everything that would fit me. Sometimes I would sleep in a night gown. I finally got some guts to buy some underthings for my self in my late teens. Then it just progress from there I bought shoes and everything else.
I got a very late start. I had no sisters and one brother. I was attracted to girls, not boys. My first glimpse of Laura was when I was a young teen riding my bike in cold weather with my hood up and a man on the sidewalk gave me a wolf whistle. It was a thrill but I didn't quite understand why until I was in my 20s, very lonely, needing a girlfriend. I discovered I could be one.
I got started kinda late, at age 12, trying on my mothers nurses outfit (sure do wish I could find one of those on ebay),
her two inch pumps and her satin front long leg panty girdle..Try as I might (or might not) I cant get that image out of
my mind. Thrillingly, intrigue, adventure and suspense. I just don't understand why every man alive don't at least
try crossdressing once in a while..
love you, dana
Not until I was in my early teens. Most favourite outfit was a cream long sleeve angora mix sweater with a tan coloured box pleat mini skirt, and white heeled sandals. Remember it so clearly.
But definitely not with any approval, most secret!
Christen X
I am told i was put in a lace baptism gown when i was just a baby. Obviously i have no memory of this nor do pictures exist. I dressed on my own when i was a teen in my mother's stuff.
I hope you post the story of that summer one of these days!Originally Posted by Krystenw
I have pics of my mom dressing me up afew times when I was really young. My sister dressed me up when I was about 6, then I had a girlfriend in high school who helped me experiment with her clothes. One day I went to get house while her mom was at work and she did the whole nine yards. I had longish hair and she even styled it a bit.
I remember playing "dress up" with my female cousin back around age 5-6 if I recall correctly. She used to love dressing me up in her leotards and tights like we were both ballerinas. She told her mom that I enjoyed wearing her tights and leotards and her mom said its ok since male ballet dancers wear tightstoo, so one day her mom bought me my very own tights.
I remember the first time I tried on my moms pantyhose. I was in kindergarten and soon after that I started wearing pantyhose to School underneath my jeans. At about eight I tried on my mom's bra for the first time and kept going from there. By the time I was 13 in the summer when my parents both worked my brother was outside or gone I would dress the entire day and every summer after that up until I graduated high school I spent almost every day dressed.
I don't remember the whys or hows, but I remember wearing my cousin's nightgown while staying with her. One of those flannel things with the ruffled collar. Of course my mom had a fit. I think I was maybe 4 or 5?
When I was 14 I tried on my mom's clothes, but her "fashion" taste was , frumpy? boring? Stolen from an elementary school teacher? That game lost it's appeal quickly.
But my grandma was a seamstress and used to make Bridesmaid and prom dresses, and I loved trying those on! OMG they were wonderful.
And that's the first time in my whole life I've ever admitted that to anyone.
It was the Summer of my ninth year when I was picked to be a little girl in a Scout play, because I "was the smallest and had the longest curly hair". Mother refused to have my hair cut, and was elated as she went "all out" to teach/dress me to be a girl in real little girl clothes - from silky undies to poofy lacy party dresses to MJ's and hair ribbons! Everyday for two weeks I wore girl clothes as she did my hair, polished my nails, and showed my how to add light makeup & perfume so I would think of myself as a very convincing little girl. I was embarrassed and humiliated when Mother proudly showed me off to everyone as her "new little girl".
I remember being in the Cub Scouts around 9 or 10 years old. For some reason the Cub Pack was putting on a history show and our den was to present how female clothing looked thru the history of America. Go figure? I ended up having to dress as a girl from the days of the pilgrims. Blah! I remember my older sister putting a bra on me which I pretended to hate. I also remember being so jealous of a friend who got to wear a wedding dress and had to have his hair in curlers the night and the day before the show. Why the hell couldn't that pretty girl be me?
I'm a Wendy and I love it!!!!
I first dressed as a ballerina when I was around 5. Then I always loved satin things and girly stuff whenever I saw it. In junior high and high school... it when the fire lit and that side of me told me that I was more than one person.
Remember that moment when I first wore that ballerina outfit like it was yesterday. it was such a special feeling.
Vanny
Posting Permissions
