At What Age Did You Start To Crossdress? / What age did you start cross dressing? Why

[Pretty Heather]

I had been approximately 12 or 13 - A former neighbor visited my parents for the weekend. She had been a terrific beauty!!! My mother hung some of her extra clothing over the inside of my bedroom door. Example, a silk slip, blouse, etc. I felt myself touching the fabric, then kissing the silk slip..LOVED the aroma. As like the panty / bra dresser drawer of my mother.

Would wear the form fitting bathing suits of my mother - when I had been home alone.

Nothing like the feel of a short silk slip rubbing against my panties.

I think my mother always knew, although we never discussed it (wish we had).

[Zee]

My earliest memory of crossdressing is at around age 8. Of course I was caught, but the desire to dress like all the girls was with me well before 8. I so wanted to be a girl.

My desire carried on through my childhood, secretly finding my moms stockings when she wasn't home and putting them on. I was found out only once, hording them under my pillow. Silly me, but I was young.

I got more crafty as time went on, allowing me to fall asleep in womens clothing only when I was sure to be the first one up.

I had a terrible time in puberty, getting hair in places I didn't want, watching all the girls having a great time. It was pretty lonely through school, though I had friends; I was even on the football team in high school. No one really knew, and it was a secret I carried with me. I babysat for my eldest sister who had the most wonderful and exotic costumes, I had to try every one on, and by the time I was 11, I had.

I was kicked out of my house because I got an earing in one ear (believe me I would have been ecstatic to have both ears pierced). My mother was not tolerant of that what so ever. However, it did allow me to explore my self more fully when I was out of the house. I dropped out of school and got a f/t job at 16 as a graveyard shift conveniance store attendant. I wore skirts behind the counter... nobody knew.

My sister had pitty on me, took me in and I went back to school. Of course my secret needed to be under wraps a little while longer. (And of course, her clothing was never safe, but always pristine when put back, oh so carefully).

I went back to live at home after my mother accepted me again. My father could have cared less. Went back to school and was subsequently kicked out yet again. Still, since my childhood, I had yet to be caught crossdressing.

Again, I was kicked out for breaking curfew or some minor infraction. However, by this time my biological mother found me and said I could live there if I went back to school and graduated.

Well I did, still my secret desire to be a woman remained hidden. All this time I wondering what was wrong with me. My biological mother didn't know either, but she showed me that I needed to be me regardless of what happens. It was then I found that there was, infact, nothing wrong with me.

I went to college, met my wife online. Went to the US to meet her. I was completely honest with her and she was fully accepting. I am more open about it, still the years of keeping it a secret, wearing clothing as to not show off bras, pantyhose, etc that I would wear undear my "man" clothes, is a hard habbit to break.

About 5 years ago I decided to start shaving my legs, after all, I am getting older and I really needed to be me. I keep most of my body shaved now and never had a second thought about wearing shorts infront of anyone, thanks to my wife.

About 3 years ago, I was in full dress nightly, although I always wore things under my clothing.

I have accepted that I can not be a woman, no matter how badly I want to. Early in life, I am sure my family would have never allowed me to explore or even attempt at gender reassignment. Circumstances in life did not allow for that either. Now, I have responsibilities to my kids and my wife. But crossdressing really allows me to express my self I otherwise could not.

I realize that this was only supposed to be when I started/why I started. Sorry about being long winded. Thanks for listening.

Z

[glossy]

[SIZE="3"]I was under 10 when my aunt visited us and I went into the guest room while she talked with my parents. Her suitcase was open on the bed and her satin slip hung out of the case just begging to be touched and fondled. I did and was instantly hooked on the silky fabric.
I knew this was for me and I found ways of raiding my sister's lingerie drawer. I graduated to buying my own panties when I was 20 and living on my own. When I married, it gave me endless pleasure to buy my wife silky lingerie because, in my fantasy, I was wearing it.
I remember getting out of bed one night and putting on her panties and a slippery little bed jacket which caused instant arousal. She awoke and saw me in extremis. I confessed to her my need to dress in women's lingerie and nighties. She managed to cope with this, without being terrifically happy about it. But I spent years convincing her of my love for her and not the clothing. Truthfully, however, my fetish has grown stronger as the years have passed.
Eventually, she participated by helping me buy the right sized lingerie, bras and pantyhose or stockings instead of my buying it for her and then trying to fit into it. That was a huge breakthrough.
Now we are pretty comfortable sleeping together - me in my satins and silks; she in her more comfy cottons. When we make love, she dresses in the silky nighties. She allows me to wear slippery lipstick and we kiss and exhange the lipstick lip to lip. I love that.[/SIZE]

[Robyn2006]

[SIZE="2"]The first I can recall thinking that something might be amiss with me was watching my sister get all dolled-up in her bathroom when I was about 8 years old. She was 16 at the time and quite beautiful... Well, that doesn't quite say it. She was (and is) drop-dead gorgeous, knew it, and so enjoyed driving all the guys crazy. She spent hours getting ready for her dates and just completely transformed herself into any man's fantasy there before my eyes. Watching her get all made up had incredible effect on me, and from that early age I wanted nothing more than to be as beautiful as her in every way. However, it was quite a few years later until I really gave it a shot. When I did, I was fifteen and had been stealing moments here and there to explore my mother's and sisters' things, but was only still dabbling at the venture. But truth be told, it was pretty hard, as I was hardly ever really alone, there was always someone in the house! Before this day, the best I ever had was the time alone I had when taking rather unusually long baths, no one ever dreaming of what was really going on inside that bathroom... with me trying on my various things of my sister's or mother's.

Anyway, it was a Sunday and after the insanity of church, everyone was off to do something. I FINALLY found myself really alone, and I knew I'd be alone for the entire day!!! By this time I knew where everything was and spent no small amount of time luxuriating in all that was there for me. At fifteen, with long blond hair and slight build, the transformation didn't take long, and before I knew it I was in full gala there in my parent's bedroom wearing my mother's red-flowered summer dress, stuffing full her 38D bra underneath with toilet paper, and completely indulging in all her and my sister's makeup... experiencing so much for the first time. This was the first time I put on nylons, the first time I wore mascara and eye-shadow. It was the first time I was able to try on so many different shades of lipsticks, coating my lips so glamorously full! It was the first time I really felt myself an actual girl... the first time I really felt alive. I was in such heaven, but a heaven that I felt would be the death of me if I were to be discovered. Sadly, within every moment there was fear... I was alive for the first time as a girl, but so scared... so terrifyingly scared.

I spent the entire afternoon in this newfound freedom and remember so vividly how amazed I was that there was this pretty young glamour girl staring back at me from the mirror ... was that that really me???!!

I look back to that day so often and think of it as a real watershed for me. It was on that day that Robyn was born, it was on that day when I really found who I was. And, although it has been a rather rocky ride over the years, I wouldn't change a moment of that day, its excitement, or its effect on me. I only wish I could somehow go back and tell that fifteen year old pounding heart of mine that it's ok, that there is nothing wrong with what I was doing. Were that only possible!

Robyn[/SIZE]

[vw1071]

I started by wearing my mother’s high heels when I was 7 or 8 years old.
I moved up to experimenting wearing my mother’s clothes (stockings, panties, skirts, dresses, high heels) when I was about age 12.
I really got into it at age 15.

My mother and I lived alone in our apartment, which made it very convenient for me to dress up when ever she went out.
When I was home alone, I would wear her stockings and panties with skirt or dress with a pair of her high heels.

This was my secret pass time for quite a while – secret until the day she came home early. (This is why I remember I was age 15.)

I was sitting on the couch wearing a pair of her black thigh high stockings and her pink 3.5 inch stiletto heel mules and, well, pleasuring myself.

I was totally unaware that she had come home and was watching me from the entry way.
I didn’t even know she was there until I had finished.
I’ll skip the part about my embarrassment and the feeble attempt to cover myself up.

She was cool about the whole thing.
She reassured me that she wasn’t angry and that I wasn’t doing anything wrong. She asked me if I wanted my own “ladies things” to wear.
Of course I said yes.
She took me shopping and she bought me stockings, panties, 2 pairs of high heels, 2 skirts, and a baby doll nighty for my very own.

This was the start of my adventures in cross dressing.

After that, when ever I was home, whether she was there or not, I was dressed en femme.
My ladies wear collection grew quickly, thanks in a large part from the help of my aunt (which unfortunately is not part of this topic).

This is a very watered down version of my story. There’s lots more that I would be happy to share (it’s not really part of this topic).
If anyone wants to email me at [email protected], I can fill in the details.

[Rosaliy Lynne]

Anyway, please advise at what age you were when you first started to cross dress and how you felt. Did you continue or stop for awhile? What articles of clothing/makeup did you start with? Who's clothing was it?

I started at 5 years old with my mothers underclothes (slips, nylons, panties, shoes) and eventually at about 8-10 years old was also getting into her dresses and bathing suits. ... FUN FUN FUN!!!

Ash

I actually started dressing just before starting my high school freshman year and the clothes weren't mine. Well they were AFTER I acquired them but ...
Anyway I, for various reasons over time, gained and tossed many suitcases, bags and boxes of womens clothing. I had everything from skirts, blouse and dresses to panties, bras and girdles. I was a full dress up girl from the start..

As an adult, when I first separated from my 3rd (last) wife, my hair was Halloween costume wigs from Walmart. They were not the best but how far wrong can a gal for for under $5 each? I finally broke down and purchased my first wig from Paul Young on line. Actually that is not entirely accurate. When my second wife was still accepting of me this way, I had purchased my first all human hair wigs. I remember the female clerk looking at me severely as she informed me in no uncertain terms, "you know these are for women!"
As long as I paid for them whose business is it for whom I bought them. Looking back NOW as I write this, I am tripped in that she clearly identified ME as the one who would wear them. I wonder if there was some invisible (to me) sign that said "Cross Dresser". Today I now have 17 Wigs, 8 of which were given to me. I lost one to a fellow CD who was over recently. I let her use it while visiting and she "forgot" it wasn't hers. Funny tho I haven't heard from her since I asked for its return. <giggle>

[KandisTX]

Today I now have 17 Wigs, 8 of which were given to me. I lost one to a fellow CD who was over recently. I let her use it while visiting and she "forgot" it wasn't hers. Funny tho I haven't heard from her since I asked for its return. <giggle>

Is SHE a member here? Maybe the rest of us can shame her into returning it Seriously though, that is just wrong to borrow something and NOT return it. I do hope you get your wig back.

Kandis

[Charleen]

Mom's high heels at 3. Clothing at about 12.

[missattitude]

It started about at the age of 3-4. I was fooling around with the laundry. Picked up a pair of my sisters tights, put them on. Ever since then I been disired to dress. The older I got, the more daring I got with it. Now I dress for self confidence and sexual pleasure. There is no other way to go to bed then with some nylons and bra
Miss Thangs

[CourtneyinTaylor]

After reading the first post on here it made me think. I remember having my aunts dress me up when I was very young. but actually digout stuff on my own I was around 12. I was caught with the stuff under my pillow, and it was dropped after that. I stopped for a lil while cause I could not get my hands on any thing for a while. My first real girlfriend I stole a pair of her panties that she never knew about and wore them as often as I could. Then got married and would still things of my wifes. Now remarried (no cding was not the reason for divorce) my current wife is totally supportive and helps me when ever I ask. For that matter she will go pick stuff out for me at the stores lol .

[surfdoc]

I can remember putting on my moms boots and my grandmother catching me... justa few laughs. I must have been 7 or so. It was right after I got caught writing with crayon all over the wall in the closet.
Ciao'

[Michelle37]

i started at 8 with my moms hiheels. i liked the way they clicked on the wood floors. by 10 i was sneaking her clothes. by 13 i was sneaking my sister makeup. by 14 all of it together made me feel very happy. kind of like xmas morning excitement. been doing it since and havent stop even though other people dont like it.

[Rosaliy Lynne]

Is SHE a member here? Maybe the rest of us can shame her into returning it Seriously though, that is just wrong to borrow something and NOT return it. I do hope you get your wig back.

Kandis

and no - she is not a member here. We'll see what happens - maybe she is just terribly busy right now. oh well

[Darlene-VA]

I was 14 and have been doing it ever since, first 2 years in my mother's and aunt's clothing and with my first paycheck started buying my own clothes and everything needed to make the complete transformation

[Val702]

I think I may have been 12 when I first fit into my mom's heels. I wore her dresses and hose. I took to walking in heels with no prob. More comfortable than sneakers. I started gettin my own stuff at maybe 15. I quit for maybe 3 or 5 years. Dressing up maye once or twice. Then I started buying stuff. I CD on and off through my marriage. Kept it outta site. Then my stuff was found. Then I came out to my wife. Ok at first, then not. Then the marriage fell apart, for a ton of reasons. Now I am rebuilding my wardrobe. I am working up to being in public for the first time. I'm so skeerd! After all I am a pansy ass sissy!

[linda1977]

My first (albeit partial) crossdressing experience was when I was 6, although I always had the urge to wear female clothes before then. This happened during a Xmas panto performance/rehersals in my infant school, where me and my friend took on the roles of "Kings of Topsy-Turvey Land" in Sleeping Beauty. We were "topsy-turvey" because the top half of our clothes were masculine, but we wore mini-skirts and pantyhose below! Looking back, I should have been embarassed about that cruel joke put upon by our teacher, but I'm not, and at that time I never felt embarassed about wearing them - in fact, I was pleased that I was given the opportunity. :D

About a year-or-two later, I decided to wear my auntie's make-up, and proceeded to display my "skills" to my parents. In fact, I looked a right mess, and everybody just laughed, but I never understood why at the time.

My first proper crossdressing experience was when I was 11, when I discovered a bag of old clothes in my toy box. Inside the bag, I found a blue dress, a green bikini set, and a pair of unworn green pantyhose. Without a moment of hesitation, I decided to wear them all (the bikini acted as a normal bra and panty), and I felt so relaxed and happy as a result. From that point on, I crossdressed whenever I could, out of sight from the rest of my family.

[MsEva]

I was fascinated and starred and starred--a boy at a school carnival had been dressed up as a sexy fortune-telling gypsy, when i was age about 9. (No insult intended to real gypsies.)

Again about age 12 on Halloween school party day. A classmate Peter (whose mother was a beautician) dressed him up beautifully as a woman, black dress, wig, heels, purse. We all thought he was a substitute teacher. I was so interested, i couldn't take my eyes off him. Jealous, yet to scarred to try any women's clothes myself--until a year later in the privacy of my mother's room.

Very similar experience. I guess I have always known that I fancied female attire. Something just clicked. I was around five or six and my brother was serving in Vietnam, sent back a vietnamese doll. She had on a long silk dress. Used to play with GI Joes *couldn't you just die? with her. She was a spy trying to lure the poor Joes into traps. I identified with her, not the male doll.

One Halloween, while I was in fourth grade, a third grader dressed as what I can only say is a blond bombshell. She or he had on a tight skirt, blond wig, black boots, full makeup, and I couldn't take my eyes off of her. I wanted to be just like her.

Later, I always was in awe when Mom took me to the department store and she got to go into the Ladies Lounge. I had to wait outside and watch the beautiful ladies coming out after fixing their makeup and perhaps a cigarette in the lounge. It was like a mystery wonderland. Later I found that I had a bit of a foot fetish. I could fit into my mom's go go boots and did. White with some sort of embroidered piping as well as a black pair with similar piping. That was around the age of 12 or so. Later, around 16 I discovered that our friends who previously owned our house had a truseau in the attic. In it the daughter had 2 corsolettes or actually merry widows that I adored wearing. She would visit off and on and kept a stash of makeup that was fantastic. I spent my late teens delving into her makeup and the merry widows. I think I was set at that point.

[Karlie]

I guess this is also another way to introduce myself to the forums. I started, not of my choice, when I was about 3 years old visiting with my parents at my aunt's home. My parents weren't ready to go home but the decided it was time for me to go to bed and I was put in my female cousin's nightie. Kicking and screaming. As I grew up and before 1st grade, I played with a boy across the street who had several older sisters. He introduced to me to their clothes ! We'd play in a few things from their closets. Never got caught. Lots of experimentation over the early school years in my mother's stockings, garter belt, heels and slips with great excitement. In 1968, my family visited an aunt in California, and I slipped into her bedroom one day and went thru her dresser and found my very first pair of pantyhose. They fit wonderfully and I was then hooked on those for the rest of my life.

Combination of factors that got me started, but I can recall lying on the living room floor watching tv, with my bare legs exposed and yet another aunt and my mother commenting on my pretty legs. Seems, my aunts were always around for some seminal event, doesn't it? I recall praying at night, when I was a little boy, that I would wake up a girl. Never happened! There was also a Christmas play in the second grade and I drew the part of a cow. Had to be dressed up in red clothes and needed to wear red hose or tights. One of the girls in class brought a pair from home for me to wear. Right into the classroom. As the class was getting ready and dressed in the classroom, the teacher told me to go behind a cardboard display and put the hose on and get dressed. You can guess the rest from that. I seem to have been pushed and directed to cross dress all my life.

Now, I am retired, and have a trunk full of nice things. Have had several discussions with my wife over the years but it came to a head two months ago and a compromise was worked out in that I will dress and she won't know about it.
I can live with that for now.
Karlie in Memphis

[Rosaliy Lynne]

I would sit or stand next to her, utterly entraced. When I was about 3 or 4 she was putting on lipstick. She turned around (she must have been watching me in the mirror) and carefully put some on my lips then carried on getting ready.

From time to time when she painted her nails, she would ask "do you want some" and would paint my nails and toe nails. It was so "matter of fact". She must have sensed I wanted it and just did it without comment or fuss. then I would carry on playing or doing whatever I was doing.

She gave me one of her old lipsticks to play with and I would put it on sometimes.

PS

I am still fascinated to watch a woman do her makeup.

What a delightfully easy acceptance she instilled in you. Yeah MOM!! Not many of us had that easy an intro.

I think I may have been 12 when I first fit into my mom's heels. I wore her dresses and hose. I took to walking in heels with no prob. More comfortable than sneakers. I started gettin my own stuff at maybe 15. I quit for maybe 3 or 5 years. Dressing up maye once or twice. Then I started buying stuff. I CD on and off through my marriage. Kept it outta site. Then my stuff was found. Then I came out to my wife. Ok at first, then not. Then the marriage fell apart, for a ton of reasons. Now I am rebuilding my wardrobe. I am working up to being in public for the first time. I'm so skeerd! After all I am a pansy ass sissy!

Looking forward to getting together and let you know that you don't have to be afraid to be out in public as the woman you are. After you get over that hurdle it gets better and more fun.

My first proper crossdressing experience was when I was 11, when I discovered a bag of old clothes in my toy box. Inside the bag, I found a blue dress, a green bikini set, and a pair of unworn green pantyhose. Without a moment of hesitation, I decided to wear them all (the bikini acted as a normal bra and panty), and I felt so relaxed and happy as a result. From that point on, I crossdressed whenever I could, out of sight from the rest of my family.

If they were in your toybox, someone obviously knew you needed them and wanted to let you know it was ok without making you feel self-conscious. Way ta go!!!

I guess this is also another way to introduce myself to the forums. I started, not of my choice, when I was about 3 years old visiting with my parents at my aunt's home. My parents weren't ready to go home but the decided it was time for me to go to bed and I was put in my female cousin's nightie. Kicking and screaming. As I grew up and before 1st grade, I played with a boy across the street who had several older sisters. He introduced to me to their clothes ! We'd play in a few things from their closets. Never got caught. Lots of experimentation over the early school years in my mother's stockings, garter belt, heels and slips with great excitement. In 1968, my family visited an aunt in California, and I slipped into her bedroom one day and went thru her dresser and found my very first pair of pantyhose. They fit wonderfully and I was then hooked on those for the rest of my life.

Combination of factors that got me started, but I can recall lying on the living room floor watching tv, with my bare legs exposed and yet another aunt and my mother commenting on my pretty legs. Seems, my aunts were always around for some seminal event, doesn't it? I recall praying at night, when I was a little boy, that I would wake up a girl. Never happened! There was also a Christmas play in the second grade and I drew the part of a cow. Had to be dressed up in red clothes and needed to wear red hose or tights. One of the girls in class brought a pair from home for me to wear. Right into the classroom. As the class was getting ready and dressed in the classroom, the teacher told me to go behind a cardboard display and put the hose on and get dressed. You can guess the rest from that. I seem to have been pushed and directed to cross dress all my life.

Now, I am retired, and have a trunk full of nice things. Have had several discussions with my wife over the years but it came to a head two months ago and a compromise was worked out in that I will dress and she won't know about it.
I can live with that for now.
Karlie in Memphis

She may come around in time. Take it slow and easy like any other part of your relationship. Good Luck.

[sissy_tulsa]

I started dressing when I was like 10-11. I wore lingere from my sister and my mom both. It was something that I did every once and a while, mainly to masturbate. When I got older, 16-17, I started going to adult lingere stores and grabbing what ever I could, run up to the counter and pay for it and leave... THEN I would see if I got the right size-lol. Now that I am older, I have friends that I go shopping with and buy the right sizes and styles!

[Val702]

I first tried stuff on at the age of 8 or so but I did not start "crossdressing" until I was about 12. At that time it was used as a shield for me because I wasnt a popular kid in school so when I was home I dressed to "get away" from my problems. As I did this more and more I felt more and more comfortable doing this and it become more of something I loved to do for fun and simply because it felt great.

Word!

[Delia1]

I was in my early 20's. My girlfriend, now my wife remarked that i needed to go on a diet and get rid of the bit of beer belly which i had got. I remarked it was ok for her, she wore a pantie girdle that kept her looking trim, men cannot do that. I never thought much more of it, but next day when i was getting dressed, she said stop, i have something for you to try. With this she produced a pantie girdle, i was lost for words. Anyway she made me get it on, which was a struggle, but i must admit the end result looked good. It did slim my tummy down. But the biggest surprise that happened, is i found out i enjoyed it, i felt really good, and cannot really describe the feeling. My wife tells me now, that she caught on quite quick that wearing her girdle was turning me on. And a few night later in bed, she said your skin feels all hot, why dont you put on of my nightdresses , it will feel cool on you. I did not say no, and again really felt at home wearing it. But to cut a long story short, i now wear female clothes 70 percent of the time,. I am lucky to be able to work from home, so can dress as i please. As i type this, i am working at my dest in a skirt and top, pair of lacy panties and bra, sheer tights and high heeled shoes, with full make up on. I know i am so lucky to be able to have a wife who not only understands but enjoys me when dressed in the female role. Anyone who cares can private message me if there is anything they need to ask.
Delia

[chrissietoo]

[.i am so upset beacause i have not pics when i was child or teen dress as girls.is somebody who have pics when was child or preteen CD?.If have somebody pics with child young CD
please put

This line makes me a bit nervous.[/QUOTE]

I'm grateful that have a few precious pictures of me at age ten dressed as a girl on Halloween. I have to say, I was very pretty, and my face and expressions are totally sweet. I had no trouble being a girl.

There is also a funny set in kindergarten, when the class all dressed up and posing for a group photo, and I was tugging and touching the frilly dress of the girl next to me....hmmmm what was going on in little chrissie's mind???

[Rachel32533]

It was early... I have a twin sister and I remember wearing her cloths very early. Mon would often put me in my sister's cloths if mine were dirty. My first memory is about five went my mother dressed me in one of my sister's dress including panties and shoes. It felt great, and I wondered why she always got the perty cloths? It continued until I was about 12, I even had to wear her panties to school if mine were not clean. One day went I was in the 4th grade I had on my sister's panties at school and I knew something was different! I then started wanting to wear her cloths more and more. I was the same size as my siter and we looked identical. I continued wearing her cloths all the way through high school. When the family was gone I would change into her cloths and put on my mothers wig and cruise around town. Often people would confuse me for my sister. My desire has never gone away. I still dress as often as possible. While my sister knows about my crossdressing I have not brought it up to her in many years and she has not asked. I am certain that the desire starts early, and will never truly go away.

[mackemlass]

My earliest memories are of wearing Mum's tights/pantyhose when I was around six or seven,though I have no memory of how I came to start wearing them. She had a pair of brown knee high boots I took a liking to as well,the first time she found me wearing them she said "What ARE you doing"? Said I was just playing and she didn't seem to mind,after that it was "You wearing my boots again"?. She didn't know about the tights though and had a different attitude when she eventually caught me wearing them and said it had to stop. I'd outgrown the boots by then and just started being more careful.