First Time

[thecddj]

Hi all,

What was it that made you try your first item of women's clothing on ???

[Vanessa_V_Ed]

My case was jokes on freshmen at university.
There were a couple of residences one for boys and one for girls.
One of the classical nights out was about switching clothes, just a skirt and some makeup for boys and beards painted on girls.

[Sarah-RT]

I cant recall exactly the first article of clothing i put on but I remember cross dressing an action figure one time as a child when i was playing with friends who had barbies, the why of that i don't know. One of those friends on a different occasion was at my house and I can remember asking her would she show me how to put on my sisters lipstick. Again, the why of it or what I was thinking I don't recall but just the desire to do it.

What about yourself?

Sarah x

[jenni_xx]

I was either 5 or 6 years old. I was forced to wear earrings by my sister and two female cousins. And then I was marched out to "present" my new attire in front of all of our parents

The first time I myself made the choice to try on an item of women's clothing was around 8 or 9 years later. A skirt that I put on over my school trousers.

I still wonder to this day what it was that made me feel compelled to do what I did. I have no idea what it was. All I know is that I had a compulsion to try it.

[jigna]

I wore my sister's frock at the age of 5 and Journey started from there.
this was followed by wearing ladies under garments.
Continued even after marriage.

[Robyn2006]

Posted this earlier, in a similar thread.. Found HERE (http://www.crossdressers.com/forums/showthread.php?187692-When-did-you-first-crossdress&p=3071257&highlight=#post3071257) :kiss:

[thecddj]

For myself i was about 4 and it was winter, was cold in bed and i put my sisters slip on to keep warmer, it felt amazing next to my skin, then a few years later i used to wear my sisters silky dressing gown around the hose in the winter and progressed to wearing her undies.
soon as i was able to i started to buy my own and now need a new wardrobe to fit it all in !
:)

[Meganfla]

I lost a drunken bet amongst close friends (male and female), had to put on some lingerie and serve them all drinks.

[reb.femme]

The soft and silky feel of my mum's waist slip was definitely my first hit.

Still love soft materials next to my skin.

Rebecca

[thecddj]

Still love soft materials next to my skin.

Rebecca

Same here, most of my collection is soft and silky.

[jennifer1958]

A pair of my sister's green cotton panties sitting in front of the washing machine when I was fourteen. Jennifer

[Sarah Louise]

My mum's tights when I was four. My older brother suggested we wore them (he was six) and show our parents who laughed. I did it again on my own a couple of days later hoping to get the same reaction, but my dad just shouted to get them off. Any amateur psychologists want to speculate that this has led to the desire to cross dress?

[Jennifer B]

@sarah7391: That's amazing I had a very similar experience at a very similar age. I put on my Mothers tights and started dancing around the house, which had everyone in the family in stitches. Until it went on too long and my Father pulled the plug on the fun.

Nothing like that happened again until I hit puberty and then I was in and out of the washing basket like a jack in the box "borrowing" my Mother and Sisters knickers and slips.

[sometimes_miss]

The very first time was when I was a toddler, my mom dressed me in my sister's old clothes, supposedly to save money so I wouldn't ruin my 'good boy clothes'. I wasn't old enough to know any better so I didn't associate anything to it at that time. The first time I did it to myself, was when I was a little older, and every day my mom spent a lot of time getting my older sister ready for school, and all the fuss about how good she looked before she left the house. Mom never went through any trouble with me, and never told me how good I looked. So I went up to the attic where I knew my sister's old clothes were stored and put on some of her old clothes, went downstairs and told mom I was ready to go to school too. Of course she changed me back, after we took sis to school, mom asked me if I really wanted to wear her clothes, but in such a way as to infer that my answer should be no. So I told her no, and didn't do that again. The next episode was when I was molested, and my abuser suggested that god made a mistake, and that I was really supposed to be a girl. Initially I was confused, it didn't seem right, but as I looked at the past times when I was dressed as a girl, and then other things that supported his idea, it all seemed to make sense. Soon I was dressing up as a girl myself, in secret, all with the idea that I could make god happy so that he would fix me, and my male genitals would disappear, I would grow breasts, my body would change and I would become a pretty young woman by the time I got to high school like all the rest of the girls. Reinforceing the idea that I was really a girl, and should dress as one, through all those development years apparently 'stuck', and I would feel that way for the rest of my life. Doesn't matter that all the rest of my behavior, feelings and ideas fit into the male side of the charts, the feeling that I'm supposed to be a girl persists. So, I 'go with it', and dress the way that feels normal.

[Angie G]

It was so long ago I don;t even remember what made try it but I'm so very glad I did. I found me that day.I think the first ghing I tryed was a pair og heels.:hugs:
Angie

[TrishaLake]

Very young for me...always satin like fabric ....I remember panties, slips and nightgowns....loved every minute of it...still do

[Jilmac]

For me it was a dare. My cousin dared me to wear panties and a dress when I was seven years old. I'm a senior citizen now so that was many years ago. I thank my cousin for daring me back then, but I had to stay hidden for many years due to non acceptance. Now I'm out and loving it.

[cheryl reeves]

for me it started when i was born and wore girl clothes for 2 yrs then my dad stopped it,but it was always there swiping my sis panties for we were the same size,to fantising about being able to switch genders at will,to sneaking my sis and moms dresses..for me its dresses when im dressed.

[BillieJoEllen]

I don't really know what the first item(s) were. I believe it was panties. My mother would often dress me up in my older sister's panties and tees. The first items that I was really interested in though were a nylon blouse a brown tight skirt and everything that is worn underneath. How I got there has been posted elsewhere and is kind of long. Those items markrd my arrival as a crossdresser.

[Amy Lynn3]

My mind was so young it never recorded this, but my family told me I would take my older sisters panties and wear them and then hide them. When my sister ran low she and Mom knew where to look and the routine would start over. My first memory was when I would wear and black OBG, belonging to my Mom. I still love to wear them both.:heehee:

[Amanda M]

Possibly about four. Being Scottish, I was obliged to wear the kilt at my sisters wedding. Dear Mum, made a firm decision from which she would not be dissuaded, that I must wear girls' knickers under my kilt. Despite my protests, she had her way. Now I am not sure that this led to further crossdressing, although I suspect it played a part.

Curious thought though........... If my wife asked me to waer a nice pair of panties, would I resist. Answers on a postage stamp please.

[Isabella Ross]

My mom's Vanity Fair panties and a slip. Remember like it was yesterday even though I was just 7 or 8 at the time.

[Cheryl T]

When I was young I was a bit chubby.
My mom always wore a girdle and would always say "I can't wait to get home and take this thing off"...paradox...
Then one day she says that if I get any fatter she's going to get me a girdle....enough said. I just had to find out what this was all about and why the love/hate relationship....now I know.

[BLUE ORCHID]

I'm not sure as it all started over 68yrs. ago.:daydreaming:

[NicoleScott]

Opportunity and privacy. But why did so many of us "just know" to do it secretly?

[LisaKarenAZ]

It was a long time ago, but my first recollection was my best friend's little sister dressing me up with bra, undies, dress, makeup, and nail polish, and proceeded to parade me in front of my mom and one of her close friends.

It ended up resulting in my mom telling me to "take that stuff off", which led to me thinking that it was a bad thing and I should hide it. I was hooked though. I knew from that point on, that I was different.

[Karen RHT]

I needed a new Halloween costume and found a bunch of clothes my mother hadn't unpacked from moving day. She didn't think I would wear "everything" but I did. :o

[Claire Cook]

I really don't know why. It just felt right, even though I felt guilty about going into my mother's things.

[Amanda77]

First things was my sisters outgrown panties and training bra no idea why I had to try them on but I just had to and it felt right. It just all snowballed from there.

[Karen RHT]

It was a combination of wanting to wear a Halloween costume I'd never worn before, not be recognized, and innocence. I'd never worn anything "femme" previously, had never heard the term "crossdress," nor was I aware there was any "taboo" associated with doing so. To me at the time, dressing as a woman was merely taking advantage of some readily available clothing that would effectively disguise me for the upcoming Scout Halloween party. My goal was merely to "keep 'em guessing" as to who I was as long as I could.

[Beverley Sims]

Curiosity. :)

[cdtraveler]

What triggered my fem desires was a teacher who put lipstick on me fora play. I was maybe 7 at the time. She wore a lovely perfume and t9ld me in the most sincere l9ving way how pretty it made me l9ok. I was hooked instantly on the feeling that gave me and next afternoon I was in my mom's dresses putting on lipstick and wearing her panties. Never stopped.

Amanda

[Chantel Lacey]

It all began for me on a lonely day in the middle of winter alone on the farm.,. my parents often left my alone on the farm an go to the city for a couple weeks leaving me with chores an plenty of food an fire wood.,. I had a race car set I wanted to find just to play with the toy cars.,. we had no electricity so I could not operate the track, an my parents had put it in the attic for safe keeping.,. there were so many boxes of stuff to go through to find.,. boxes an boxes of clothes.,. I spent hours looking for the toy to no avail an grew tired I open boxes of clothes around me so I made a make shift bed on the spot thinking a quick nap then I will continue looking for my toy car set.,. The feel an smell of the clothes was got me interested.,. as I looked a corset I thought this would fit me once I had it on an it fit great I was hooked.,. I loved how that material felt on my body,., I tried on every thing I could find an totally forgot about my race car set.,. I dressed in these wonderful clothes every day my parents left me alone.,. I loved to wear lingerie the most.,. any thing tight to the body.,. like a second skin.,. I had golden yellow incredibly curly hair an brilliant blue eyes, both my parents said so many times I should have been a girl,.,

[MssHyde]

I think the devil made me do it😈

[Jessica5536]

I started sneaking my mother's dresses when I was 8 or so.
I don't know why I started doing it, there isn't a specific thing I can remember that triggered it.
My family never (and still doesn't know).

[Ally 2112]

I remember the first time ( about 11 yrs ) although im not really sure when the urges started .It just got to a point where i could not help my self and had to try on one of my moms dresses .From that point on i was hooked

[Georgina]

In the late fifties we got a new young teacher who wore petticoats that were fashionable at that time. When I saw them, on a windy day, something happened inside me and I knew I wanted to wear petticoats. I searched through my mother's closets but never found any petticoats. I did, however find her slips, and I have worn them ever since. I do not know what drove me but I have no regrets.

[Michala]

Can't remember for sure but i think it was one of my mom's bras. That led to her slips and hose. The kind of hose that needed a garter to hold them up. Eventually a dress and nightgowns. not sure if she ever suspected, if the did she never mentioned it Tried my sister's bra but it was too small. Wore my mom's clothes many times when home alone. Also tried her makeup but found it hard to remove without leaving traces.

[NoraTV]

Hi all,

What was it that made you try your first item of women's clothing on ???

It was a pledge party at a fraternity, where the pledges were supposed to be "dates" for the brothers. The whole transformation experience was a revelation. That night I discovered an exciting part of me, dancing with my "date" and even getting involved in some wildly drunken making out (not quite to the level of sex).

[Tina B.]

I was around 6 years old, went to take a bath, and there on the inside of the bathroom door was my older sisters full nylon slip, of course back then it came in one color, white, at least that was all I ever saw in our house. I looked at that slip, and it called out to me, it was so long ago, I don't remember just what it said. But I do know the last words where "go on, you'll like it", and I did.
But I think Nicole brought up a great point, how did I know after I got out of that bathroom, it was best to keep it to myself, not sure, but I knew. It was a couple of years latter that I got caught by my father, he reaffirmed it was a smart idea to keep quite, I never let myself get caught again. But of course it really didn't stop or even slow me down from dressing every chance I got.

[Angela Marie]

I remember trying on my mothers tights and loving them.

[Ceera]

Hard to recall for sure, since I was pretty young at the time.

When I was about six I got moved to a 'new' bedroom in the basement of our home, so I didn't have to share my old one with my infant sister (5 years younger than me). My parents converted a bedroom-sized laundry room into a third bedroom, and moved the laundry pair to one end of a 'party room' that was also in the basement, on the other side of the basement stairs. I thought that was great, because I had my own bathroom down there, and I had a lot more privacy. Everyone else was upstairs, and didn't come down to the basement except to wash and dry clothes. If anyone wanted me, they would use an intercom from the kitchen upstairs to my room that my dad and I installed, to ask me to come upstairs, rather than coming down to look for me.

One morning - I can't recall exactly how old I was at the time, but possibly nine or ten - I was up quite early and getting dressed, and I realized all my underpants were in the laundry. Mom had done the laundry the night before, but had left the last load of white clothes, including all of my undershorts, running in the dryer, intending to deal with them in the morning. I walked naked into the laundry room to get my part of the laundry to fold and put away, as well as what I needed immediately to wear. Well, it was a cold morning, and no one had gotten up yet upstairs and turned the thermostat up, so I turned the dryer back on for a few minutes to warm up my undies! When I started to take clothes out to sort out mine from everyone else's, the first thing my hand pulled out was one of my mom's half slips that was in the same load. It was warm and silky feeling, and I tried it on to see what it felt like. Didn't fit my waist, of course, but I held it in place and loved how smooth and silky and warm it felt, especially as it slid across my naked skin! I seem to recall I looked curiously at some of my mom's other underwear - bras, panties and girdle, but I didn't try them on. Then I put on my nice warm T-shirt and undershorts, put everyone else's clothes back in the dryer, and took my armload of warm clothes to my room to fold and put away before I finished getting dressed.

That was the start of several curious investigations of my mom's clothes in the laundry. In later years, when I got closer to my mom's size I tried on pretty much all of her other things. My sister was always younger and smaller than me, so I never tried on her clothes. I don't recall ever trying to wear any of mom's clothes for more than a few minutes, and never tried wearing a purloined item under my boy clothes, or keeping anything from the laundry that wasn't mine - clean or soiled.

I don't clearly recall ever playing 'dress up' with the girls I played with, including my sisters and cousins. I may have tried on some girl things with them, but if I did, I don't remember it. I vaguely remember dressing my little sister in some of mom's things, but not putting anything on myself.

That privacy also later allowed me to play with mom's lipstick and wash it off again without getting caught. Didn't do that often, and I can't recall playing much with other cosmetics.

[Ricki_X]

When I was 10 I was caught wearing my sisters undies, I got a really bad beating of my father and kept it a to myself after that. Of course I realise now wearing a slip under your trousers does not look good!

[Mayo]

When I was around 8 or so I tried on some of my mother's underwear and a bra. At the time, however, it didn't make any particular impression on me. Since my teens, though, I've always felt as though I'd have chosen to be female if I'd been given the option (not quite the same as feeling that I am female, I realize). It's only in the last year that I've acquired any women's clothing, and only a couple of months since I've begun dressing regularly.

[Sandie70]

I was so young, it didn't have anything to do with sexuality more than curiosity. From the time I was six when my mom stopped dressing me like a girl and my dad took me to get my hair mowed off, I would watch my mom dress and explore her closet when she was away. I was fascinated with the gadgets... girdles, garter belts, stockings, bras, jewelry, makeup, high heels and on and on. The more I explored (once putting on her heels and some of her lipstick) the more fascinated I became - secretly wondering if my little girl friends knew about all this stuff. All this was such a mystery, and after a while my boy's life seemed quite dull.

I wish it hadn't taken so long to rediscover the joys of dressing.

[heathr1]

My first fem item was a girl's blouse mom bought me. She said she bougth it my mistake, thinking it was a boy's shirt. The first item I tried on through choice, years later, was mom's leather mini skirt.

I saw it hanging up and adored the look, texture and smell of it.

[Mark/Rebecca]

I think what made me was that I have always admired and respected my mother more than my father or any other male.
I have noticed I still tend to admire primarily women, and on rare occasion fall into crushes with them.
I would love to have had an adult relationship with my mother. I believe she would've become my confidant.

[Bobbi46]

Many years ago feeling unloved and unwanted turned me somewhat from the guy mode and I started to wear a half slip when on my own and at night which gave me comfort and now life has turned full circle and I can dress all the time when and how I want and feeling feminine is very calming. Also I find it easier to talk girls than guys.

[lily1974]

Being the youngest with four older sister I kinda had no choice to wear womens clothes. My sisters would dress me up during the summer to practice their makeup skills and such. Oh those were fun times. One of my sisters still has a picture of me on her wall dressed full out next to my best friend who was also dressed. I remember my dad getting pissed and telling them never again. It broke my heart but I stopped for a while till I was in my 20s. Then it was an off and on thing until about a year ago when I started doing it all the time again.

[AutumnCD]

My mom used to keep pantyhose lying around the house from time to time. I was always curious about this piece of lingerie, it was so soft and silky. When I tried them on for the first time, it pretty much started my crossdressing journey. I loved the feel of the nylon fabric against my skin. Now I always wear pantyhose when I crossdress. I sometimes even wear them under my "normal" clothes :).

[St. Eve]

Not sure the first time I wore my mom's panties. She was the only female in the house so her clothes were the only ones available. I know by the time I was 4 or 5 I was fascinated with her panties and bras. By the time I was 8, I was putting on her panties from the clothes hamper in the bathroom and sometimes taking them to bed with me. By the time I was 10, I had tried ALL of her clothes on. I had too much alone time in the house as a youngster....peace, St. Eve

[beth_myer]

I think what made me was that I have always admired and respected my mother more than my father or any other male.
I have noticed I still tend to admire primarily women, and on rare occasion fall into crushes with them.
I would love to have had an adult relationship with my mother. I believe she would've become my confidant.

I feel the same way, only the other way around because I'm FTM. I remember watching my dad get dressed and thinking he was a sharp dresser. He taught me how to tie a tie once, which I have more recently become very thankful for. I admired him. I also remember wondering why I never admired my mom in quite the same way. My first male article of clothing that I had to have was my varsity jacket. The girls' jacket was ugly, so I just got the boys' one. This was all after he died, though. I wonder what he would have thought.

[alwaysinhose]

A neighborhood girl and I went to play dress-up and she showed me how to put on pantyhose. My toes touched that silky smooth nylon and my life changed forever that day.