When Did You Start? And How?

[Guest Haily]

So I'm just wondering when did you start cross-dressing? And how did you get hooked?

Me I started at... Age 5-6 (Yes young). I wore some of my sisters dresses and then I started again at age 12.

[Guest MANNYgirl]

i started at 5 my cousin told me to put her sisters clothes and i did it was a yellow sports bra and yellow panties with flowers i remember that my grandma found me using them and she got mad and my parents got mad at me

[Guest Priscilla]

I must be an arch-latestarter crossdresser. I didn't start crossdressing until I was about 50 years old although I had felt the desire strongly since my youth. After I married I sensed that my wife wouldn't be too congenial to the idea of my dressing so I never fully broached open the subject. As the years wore away I have secretly donned her skirts and blouses, or dresses, when she has been out of house or away from home. I didn't even have any panties of my own during the early stages. Lately, however, I have purchased some delicate panties and thongs, which I keep hidden from her eye and wear under skirt or dress when she is not at home for some time. But I don't do full make-up on these occasions. For that I go to professionl crossdressing services for a couple of hours once in a while.

[Guest rachael1]

I initially started trying on my mothers or sisters clothes when I was around 7 or 8 I guess.

I stopped doing it in my teens and suppressed the urge for many years.

Recently it has come back with a vengeance and I no longer desire to suppress my feelings and have come out to my wife, as I didn't want to have to sneak around as it made me feel guilty and took all the fun out of it

She wasn't happy about it at first but has now accepted the idea and has even gone shopping with me.

However we are still negotiating on parameters, but i'm gaining more ground each day.

Rachael

[Guest Marci]

I started cross dressing when I was 12. Fascinated by woman's clothing especially pantyhose and shoes even earlier than that. My dad had a box of old woman's nylons that he used to tie up plants in the garden. I was able to raid that without anyone noticing. I branched out and eventually started wearing my sisters cloths from time to time. I've gone through various cycles of purging and returning over the years. Now the desire has come back with a vengeance and my wife has gradually grown accepting of it over our 22+ years together. I feel so much more complete if I can have my fem time.

[gennee]

I started dressing three years ago at age fifty-six. I didn't know until a counselor revealed it to me. I always felt that I was different but didn't know why. When I put on my wife's skirt, the chain of events were set in motion where today I am a happy crossdresser.

Gennee

[Guest erica2054]

i started wearing my mom bra and panites when i was 6 -0f course i didnot know what i was doing - but i know i enjoyed wearing my moms lingerie - and slow progressed to wearing my sisters=

[Sally]

I started at around 5 or 6, with stockings (remember them?) that my mother kept for sewing projects, they all had runs and until I reached my teens - they all had seams! I was thrilled when she atarted wearing seamless stockings - it wouldn't be long before I could wear a pair! Then came pantyhose! When I was finally old enough to drive I bout my own pantyhose and panties, then soes and bras and skirts - you have the idea! I became very fond of leotards while I was in college. I discovered that I was more interested in what a girl was wearing than I was interested in her. These thoughts frightened me in the days of free love (unless you were gay and then they beat you up), I couldn't count on these people to understand a cross dresser or worse - a transsexual, so out went the whole wardrobe. I built up a nice wardrobe - started feeling quilty and through them out several times. Armed with the 'knowledge that true love would cure me', I got married and a few years later I have told my wife that I am a transsexual and I have begun transitioning. She is incredible and I guess we are headed from married couple to lesbian couple if you are looking for labels.

That's my story,

Sally

[Guest DeanoCD]

I started crossdressing early this year, I don't know why I did I just got an urge to crossdress and after trying I really like it.

[Guest georgebot]

I remember starting young, as a child, before i even started school i think. I started by wearing my sister's underwear. for the longest time it was just underwear. I did not wear other garmets till i was much older. Sometimes dressing in women's clothing brought about sexual feelings, feelings which developed into fetishes over the years. Though, these sexual feeling are not what started my crossdressing, or what had kept it going. I did not understand why i did it, which is probably why i developed feelings of shame... feelings that are still with me to this day.

I am still confused about it to this day, but at the same time it makes sense. Women are so beautiful, everything about them. I like to draw the human figure, and women are my favorite subject. Their bodies combine elements of sex and love and innocence together, something so beautiful words could never describe what i see in their figure. Everything about the way they look and the clothes they wear attracts me, both physically and mentally. I am sexually attracted to women, but that is not what attracts me to Crossdressing.

I have spent the majority of my life feeling ugly, hating the way i look, hating myself. Dressing like a woman makes me feel closer to that unreachable beauty, which i know i will never completely know or understand.

[Guest Sheila]

I was 5 years old wheen I wore my first dress.

[Guest anna123]

I started when I was about 7, but that was just with shoes

I started again full on middle of last year

[Guest kris devereux]

well the first time i went to college i started crossdressing but i just LOVED it the way it felt, & i felt so feme

[Guest caroline]

well i started when i was 4 or 5 when my sisters would dress me up. then i would go and take there clothes and wear them secretly. i was caught when i was about 6 or 7 and stopped dressing for a year or two. i then started a collection of their clothes in a shoebox under my bed. which my mom found and left me a little note. boy did that give me a scare! ive been dressing on and off until this past year or two ive really felt urged to. these are often fueled by sexual thoughts which i am ashamed of. i turned 16 4 months ago and still havent found the courage to go out and buy my own clothes. being 6'3" with a shoe size of 14 makes it extremely hard cause i love shoes! they are my weakness!!! hehe. yesterday though i was given quite a scare. i was wearing a dress with my mothers lingerie underneath in flip flop heels that i hardly fit into. my mother came home and i was in the restroom. i was scared out of my wits. i had left everything out in here room and my sisters room. she went outside and i made a mad dash! i dont know how i wasnt caught! ahh i was so scared!

[Guest pip]

Hi my name is Pip i am new to this site have looked here a lot of times but never registered

Well here i am!! I think i started at the age of 12/13 (sisters clothes and my mums) and have hid my emotions since then.

Going off and on and throwing things away (like we all do)

Now iam 38 divorced and living in spain with a new girlfreind and have opened up to her about cd but still find it hard to talk to her as i have not told anyone for the last 25+ years

Thats me for now will post more later

[Guest Michelle_Belle]

I started to crossdress when I was in my early teens.

[Guest Amanda L Richards]

Hi,

Iam new to this forum. I would like to participate in the question as well.

I was about 12 when I really developed a serious attraction to dressing like a woman. I technically started when I was maybe about eight years old but that so off and on that the lack of consistency couldn't be considered serious.

At 12 though the desire was so strong that I was occupied primarily with looking at girls clothing and how I thought it would look on me and wishing desparately that that could be me instead. Occasionally I would get my hands on a pair of panties and that would be my most prized possession.

Throughout my life I had such a strong desire to dress and look like a woman, that because of the people that I knew and the types ofjobs I had, I couldn't come out. I had to do it secretly. One day I got real sick an tired of tryingto hide it but still not wanting to come out completely, I compromised.

I started to wear panties under my male clothes full tiime. Whoa!! what a difference in me did that make? I found out at that time that this was like a pressure relief valve for the urges. It seemed to calm the urges down quite a bit knowing that even though my outside attire wasn't female at all, I new that I was wearing panties "under my clothes" just like any other woman.

Of course I had to get over the fear of being discovered but that eventually took care of itself with time when no one ever suspected, and even if they did, no one was saying anything.

That was a life saver for me. I soon felt more comfortable about going to bed wearing nighties and panties and snce then it has become so natural and comfortable , that I don't worry about it not being normal. Hopefully that makes sense to you.

[Guest Kristin318]

I am new to this forums too.

I guess I started when I was seven. I tried on my mother's white front closure bra and a pair of her satin panties with a plaid knee length skirt and white blouse. I would do this whenever I was home alone. We had a pool in the back and sometimes I would try on my mom's bathing suits and go for a swim.

I stopped dressing in high school as I was too busy with marching band, sports, keeping a 4.0, and academic teams. It started up again with a vengeance during my undergrad when I got my own car (my little sister and I shared one in high school). I was dating my wife at the time and she went to school in South Carolina while I was going to school in Indiana. So, for driving breaks I would stop at lingerie shops on the way. I picked up some really cute and sexy lingerie from these stops (teddies, corsets, bustiers, g string bikinis, thongs, etc). My wife did not this at the time as it would be sometime before I got the courage to tell her. When I got to grad school, the cross dressing urge moved on from just lingerie to outerwear like skirts, femme jeans, blouses, shoes, purses, necklaces, wigs, breast forms and makeup. It has been in the past year when I started going out dressed, trying on clothes at the stores, and telling people at the stores I am shopping for myself.

[Guest Kelly Ann]

hmmmm...what a fun question. I'd be hard pressed for the age but it was young. Watching a couple of the girls my age dressed up playing ballerina across the street and asking my mother (they stayed at home way back) why girls got to wear all the nice clothes. She took it in stride and said something like 'no particular reason' and left it at that. Pretty soon my younger sister had a bright red pair of Danskin tights and some blue Olga nylon gym panties...which I overheard my sister say were MUCH too big for her. Strangely they seemed to fit me just as well as mom's shoes...and all the stuff downstairs in the basement atorage area. Once while being all dressed up down there I got the feet all stained on those tights with little black dots and had to wash them up, now, wanting to place the tights back before everyone got home I used a hair dryer on them, after scrubbing them up, with the feet all bunched up and wadded around the end. Golly they sure did dry quick...holy cow it sure did burn a major hole in one foot and melt part of the heel of the other...I smelt it before I felt it. Jeeze who knew nylon melted LOL. I was perhaps about seven then and had been into mom's stockings and stuff for sometime...which is probably why the too large stuff was purchased for my sister. Eventually she 'noticed' the hole and melted heel in those tights and asked if I 'knew how it might have happened'...being a quick thinker I explained that it was probably moths and maybe we should get some moth testicles...she walked away laughing about as hard as I ever remember. This was just after Buddy Holly died and long before The Beatles....woo hoo the 60's were on their way. I was so busted so many times back then...and never put upon by the folks or relations...it's probably the best thing that ever happened to me. It's a great thing to 'pass along'. Hugs, Kelly Ann

[Guest jemima]

Like so many here I recall the desire from a very early age to wear shoes and clothes normal for any 4 year old, but it never left me, I went on to wear undergarments of the control type and loved the feeling of being dressed up. I recall at about 12 going into an underware shop & buying stockings, bra and susupenders and wearing them when I could find time alone. I recall hidding them under my matress and being caught, gult and religious pressure caused me to begin to hide and stop my desires, I began to try and supress my feelings that made me feel unhappy and slowly I hated mself and put lots and lots of wieght on. now some 30 years on I have come out and shared my feelings and opened up a whole new freedom to be myself and have been out to buy plus size 32 bbw clothing that fit gosh I am so lucky to have found a girlfriend after a marriage break up that supports and loves for what I am. I recall the hurts of being a teenager forced to deny and conform, to those of you younger I so much understand the feelings of feeling alone, we never had the Internet, here is a wonderful place to open and find hel and support

[Guest debbie s]

Well I started in my teens when left alone at home and found myself trying on my sisters things. I found it so exciting and knew how wonderful it was to look at act like a girl. I suppressed all this until I was in my twinties and had a resurgence of desire. I bought lots of clothes from thrift stores and wigs in hollywood and found myself dressing with frequency and loving being debbie. Then I discovered my desires to reallly be with men as a date than woman. Mostly came on by going to the t clubs on weekends. Things evolved and now at 35 find myself so happy in my persona of debbie just want to be this way fulltime. I am so much happier and still evolving and considering hrt and transitioning but wory about family and work as most of you do. For the past 10 years now I see myself as debbie and so much more natural and enjoying life. My apartment is decorated very fem and one would never guess a guy lives here.I adore shopping and doing things now with my tg sisters who are so understanding.

[Guest plym]

Hi All,

I started about the age of 10 with my mothers panties and i loved the sensation, I started wearing every single time I can since then until i was able to buy my panties and stuff.

[Guest peterredbike]

So I'm just wondering when did you start cross-dressing? And how did you get hooked?

Me I started at... Age 5-6 (Yes young). I wore some of my sisters dresses and then I started again at age 12.

Graet question hun , I am a new member here but have been dressing since 12yo. I was at a halloween party lost in a parlore game and the loser had to perform a task by the members of oppositte team , ofcourse it was male vs female. My task was to be transformed into a member of opposite sex by the girls and women there, including my own mom. well i was stripped totaly and dressed from panties to skirt bra garter belt nylons heels and lots of makeup. I thought that i was imbarashed but as time pssed i realized I was in heaven. The boye treated me as a girl after the innitial squeeling and laughter. i spent the rest of the evening dressed and being hugged and kissed by all boys as well as some girls was i ever hooked !!!! well i only wish i still recived similar treatment from friends while dressed it has coast me two wifes and some closet time but a gal cant stop being a gal luv all my sisters penny from ct

Edited for sexual content. Laura

[Guest Krystyna_Marie]

I have very early memories of playing with mom's lipsticks (I ruined a lot of them playing!), the little tiny fingertip-sized ones you used to see, and in walking around in mom's shoes, and hiding in her closet among her clothes. I first dressed in her panties at age 11 or 12, and then I dressed up in a skirt, panties, bra stuffed with tubesocks, bodysuit and stockings, and mom's little wig one afternoon in summer when older brother and I were home alone together - I showed him my "look", and he was horrified and angry with me. That caused me to feel ashamed, and like there was something wrong with me, and it really stifled my desires to dress for a number of years.

Later, when I was in my mid twenties and married, I was happy and content with myself again, and my wife had a gret wardrobe, including some great panties that were really too big for her - I used to sneak into her drawers and wear her undies from time to time when I was alone.

Flash forward, and when I moved to take a new job, I was alone in "corporate housing" (a hotel) for a few weeks until my wife was ready to relocate, and I found myself in and out of Marshalls and other stores buying panties, bras, and makeup, and dressing up in the evenings after work to relax.

Now, a number of years later still, and I have a growing wardrobe of dresses, skirts, blouses, underwear, thongs, camisoles, nightgowns, and a couple pairs of 3" heels. I want a pair of boots I saw at a store in Asheville a couple weeks ago that have about a 4" heel, a mid-calf sexy spiky number - maybe I'll pick them up this weekend when I'm back in Asheville!

Thanks for bringing this up, I've enjoyed reflecting on how my crossdressing has spanned my whole life, it's a beautiful part (maybe the most beautiful part) of being me

[Guest brookeg]

I started a year ago.Two of my friend whom are crossdressers talked me into it including my girlfriend Krista,I knew I always wanted to see what it is like to be like them and I said yes loving it.I knew the slogan: Can't beat them,join them worked