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Hi Everyone, i hope you are all well. A nice easy one for you here and you dont have to be super accurate. Reading peoples posts and from my own personal experience it seems that many of us started quite young. I myself began when i was around 7 years old by trying my Mums Panties on (i must have looked a sight as they were far larger than i needed)!
Love Fiona-Ann Moss xx
Hi Fiona-Ann.
My earliest memories are from sometime around the age of 5. There was a neighbor boy who was my age and lived down the street who (I suspect) also grew up to be a crossdresser. He had an older sister and we would often go into her room when she wasn’t there and play with her things, trying on her clothes and makeup. This was before I even knew what sex and gender was, so that confirms for me that being a crossdresser is something that is ingrained in many of us, it’s not a choice or a “lifestyle”.
Hugs,
Holly
My first time dressing was when I was 11 or 12 and wore one of my mother’s bras I found in the clothes hamper. I would regularly wear her bras I found there. She caught me one time but didn’t make a big deal out of it. I was hugely embarrassed at the time, but didn’t stop. I suspect she knew that and was okay with it.
I was 5 or six. I used to live at my grandparents house with my mom and other aunts. The only men in the house were my granddad and an uncle. So, you can imagine! I remember so well I used to open my aunts’ drawers, particularly for the bras and panties. I loved the texture,the cuteness, I don’t know. One of those occasions I decided to take one pair of panties and wear it. I loved to see how I looked with them on. Unfortunately, one of those early times my mom wanted to tuck my shirt into my pants and she saw I was wearing my aunt’s panties. She got so angry! And even more when I told her I did it cause I didn’t have clean underwear. She went to my drawers and showed me my own whities. It was bad.
I didn’t care, though. I kept taking my aunts’ clothes progressively. Bra, stockings, dresses, skirts…
Sometime in my early to mid teans. I used to babysit for a young couple on my paper route. The child was a toddler and was usually always sleeping while I was there. The first or second time I was sitting for them I saw a pair of pink silk or satin bikini panties on the top of the laundry hamper that was in the washroom. I remember having this inexplicable urge to try them on and have been hooked ever since.
It’s all a bit fuzzy for me. I don’t remember a lot of specific events and ages. I do remember playing dress-up and wearing a wig and a dress for fun when I was quite young (probably 6-8) but I don’t think I really started x-dressing with any intention until I was somewhere between 9 and 11. Definitely with my moms’, and later my sisters’, underthings. I remember my mom had some pale blue satin bloomers from the 50’s that I loved and then I got into the makeup and everything else. Around the same age my sister had this gold one-piece swim suit that I used to take showers in and imagine.
— Abbie 🥰
At four I was dressed up as a ‘lady’ by mum for a fancy dress competition. At five I was wearing my sisters dresses for’fun’ and in secret. And so it went on……
Probably about 10 or 12. I found old one piece bathing suit of my Mum’s in the laundry and I used to put that on with tennis balls for boobs. Not much later I would be left on my own for weekends and that’s when I “went for broke”. Bra, girdle, funny old fancy dress white wig, slips and dresses.
Eventually got cuaght by some relatives who called in one night to check on me. Got the “talking to” from my father. Typical 60’s Australian Dad. “Dont do that again son, cos when you grow up, “The Boys on The Pub” will call you a queen!!
Horror of Horrors!!!. What fate could be worse in 1960’s Australia than to get on the wrong side of “TBITP”
Caty
It is a very long time ago, but I did get into my mother’s make up at approximately age three or four. My actual main event was at five years old, when I served as a flower girl at a wedding. I recall the frilly dress, hair ribbons, black patent-leather shoes, nail polish, etc. It took a while to get ready, then there were photos.
From reading many CDH profiles and participating in many support meetings, it would seem most of us started very young?
Hi Melissa,
This was the 1950s, so my memory is a bit fuzzy. Two girls who lived across the street from me were older than me and were “mentoring” me in the female arts. So the story I was told in later years was they required an additional flower girl for a wedding, and the two girls volunteered me. They knew me well, even at five y.o. that I would not object. I was already hooked.
Hi Stephie,
Black & White photos from the 1950s, long lost to the ages and many moves over the years. Unlike today’s digital photography, those old photos never stored well anyway, unless they were kept under ideal conditions over the years. A few years ago, we found old photo albums at my parent’s house that had been kept in outdoor garden sheds over the years. The photos were virtually useless, the album pages having been destroyed by environmental conditions over the years.
Interesting they would select you as a flower girl for a wedding! Did they not have another girl available? Did they WANT to encourage you in that direction?? Sounds fortunate for you!
From reading some of the replies I am the odd person out. I started to wear my SO’s panties with her permission when I was just over 70; 84 now. Since then I have embraced CDing and have bras, wigs, makeup, etc. Only been out in public twice; with my SO to a mall. My SO is 100% accepting saying it is just clothes and I still am a man no matter how hard I try to be otherwise. Sitting here typing in bra, panties, cami and earrings while SO potters around. Best, Marlene.
Fantastic!
I have often thought that if boys were encouraged to be exposed to dressing at a young age we’d have a whole lot more crossdressers in the world! It is a shame that this seldom happens. If I had influence over a school curriculum I’d try to encourage experimentation. It could lead to decades of positive experiences otherwise missed, not to mention (too late, I mentioned it) that many relationships might be improved or even saved, or the right life partner found, if this knowledge were available and shared before the knot is tied. Of course the subject would need to be approached in a fashion which made it clear that there is nothing wrong with enjoying the sensation of female clothes. When I was young I knew without question that anything feminine for me would not be approved, so when required to wear lipstick for a school play, solely to enhance features and not to project as female, I was too embarrassed and put off by the idea so resisted it. Had anyone ever hinted that there is nothing wrong with a boy experimenting with or enjoying feminine things and that it is in fact normal and worth trying, my whole life would have been quite different.
Early sixties here. I don’t have an SO to worry about, so when I bought my first dress it was easy enough to start wearing it to the laundromat and grocery store. Things have expanded from there 😁
Hugs and Kisses,
Fredrika JonesI remember it vividly. I was 4. My aunt caught me in a department store dressing room wearing a bra. It was also the first time I experienced shame and unacceptance.
I knew I always wanted to. I remember being as young ad 4 or 5 and was always playing with the little girls. I wanted to know what it felt like to where their clothes. That didn’t happen til I was 14 when I was stuck home alone and everybody in the family was gone, sometimes for hours. I remember my sister was on a date, my family was gone. Here was my chance. I got a pair of my older sister’s panties, one of her bras, and I put them on. I felt like I died and went to heaven. It was amazing.
Hi girls,
I, like many of you have already said, was around four years old and knew I was supposed to be a girl, so I was getting into my mom’s things at a very early age. I remember going to the next door neighbors and playing in a little plastic swimming pool with their daughter Suzie, and being quite jealous of her very pretty swimsuit. I was already hooked!Hugs,
Ms. Lauren M
For me it was when I was very young. Maybe when I was around 6 years old. It all started with panties. When I was older then it was pantyhose and slips. The slips from back then were just beautiful and fun to wear. Sadly those are hard to find now. Anyways, It then progressed and progressed to dresses and makeup. When I was a teenager I had my own stash of clothing. Then when I moved out the stash grew and grew. Luckily I only went through 1 purging when I was in my mid 30s. Nowadays I have everything I need. Although I do wish I still had some of those vintage slips from the 70s and 80s.
Susan
Susan.
I liked wearing those lovely slips too as they were so elegant and feminine. When I started to get my own clothes I also bought these slips too and have a good collection. Glad I did as, like you, say they are rare now and also very expensive for the quality ones.
When I was about 12 I tried on a pair of my mum’s tights. I loved the feel of them against my legs and I was hooked. I would wear a pair whenever I had the opportunity, later trying on panties and a bra (stuffed with rolled up socks) and eventually (when I was left at home on my own for an hour or more) a skirt and blouse plus make-up.
In my later teens I started buying my own things – tights, stockings and lingerie to start with and in my 20s dresses, high heels and make-up followed, although I didn’t get my first proper wig and breast forms until my early 30s.
Hugs Karen x
I too tried on my mother’s tights. She called it a leotard. They were red. I wore them often I had my first ejaculation wearing them. I was 11 or 12. I tried to clean them up and put them back. I came home from school and found them on my bed. She didn’t say anything.
I was 28. I was dating a lovely young woman who was to become my wife. During a lighthearted intimate moment, I put on her nightgown. After the laugh, she asked if I liked it. I said no. I lied – I liked it a lot!
As it turns out my wife was and is a stylish dresser, and as I was to find out close to my size. I had a few sneaky and brief run ins with her pantyhose and a particular yellow dress during the early years of our marriage. I put those thoughts aside though, not enjoying the deception and considering it a bit of a kink and over the top.
There was a good 30 years in between those events and the next. With my wife called out of town for a few days I decided to explore once again my old fascination. I purchased some items of my own which seemed to make all the difference. I was finally hooked, and at age 69 finally embraced the fact that I am a crossdresser. With my wife’s acceptance, my femme persona flourished. A very late bloomer perhaps, but a very happy one!
I was very young. Been doing it off and on for my whole life. Nothing makes me happier. To be feminine is a wonderful feeling for myself. Wish I could always present myself that way. Someday hopefully
My earliest, rather muddled recollection would place this first experience at around 5 years of age.
I love this question. I’ve read as many answers to this question as I can find in searches.
I can recall my first time. Some friends and I were playing in the basement, and decided to play dress up. So the washer was in the basement with us, and my Mother had thrown away some old panties. One of my friends said that I should put them on, but I was thinking to myself how much I wanted to do it, but didn’t. I was scared that they would tell someone and make fun of me, after all it was the early 60’s. So that episode got me to thinking about how much I wanted to do it if I didn’t get caught. Then one day when I was about 9 years old, my Mother had washed an old fashioned girdle, and asked me to go get it, and I just had to try it on even over my clothes. That’s where it all started. After that I got brave and asked my Mother if I could dress as a girl one Halloween. She thought it was OK, and said that other people had done it in the past after I asked about it. I remember her taking me to the local small town store where she had me trying on a girls bonnet, since wigs were expensive back then. When someone else walked in the store, she said,” he wants to be a girl for Halloween”, with a disgusted look on her face. So she dressed me that Halloween in a pleated skirt, one of her orange sweater tops, a female mask, and that bonnet. I looked like a boy dressed as a girl, and felt embarrassed about it, but all I knew was that I wanted to do it again.
You would think that with all the negative feedback I got, I wouldn’t have done it again, but our compulsion to dress is so strong that here I am today.
I was about 5 years old when it all started for me, with shoes and skirts, then bras, jewelry, pantyhose, bikinis, etc. I was 15 the first time out fully dressed and on my own wearing basic makeup with neckless and clip-on earrings, and coaming my hair in a feminine way. It was during a warm summer evening and I finally felt free as my true self, profoundly liberated. I bought my first wig and handbag age 23 and started appearing as a female during the day, mostly during short days trips driving around in my car and stepping-out here and there.
I believe I was around 33 when I first dressed. I met my first crossdresser when I was about 19, and it amazed me that a boy could dress as a girl and present that way! I thought about it for years and knew I always had a desire to dress that way.
I am not really sure, but probably about 13 or 14. In the past I always said 10-12, but when I really think back, it had to be in middle school.
One day I just went into my mothers room and put on her bra and panties. I liked it so much I added her griddle with stocking suspenders and dress and a wig. I do not recall in great desire to do it, I just kind of did it. What I do remember most about it was getting excited and having my first ejaculation. It was all very confusing, because I don’t remember getting dressed as being a sexual thing, but it ended up that way. I then didn’t dress for at least 15 years, though i always had an interest in my girlfriends wearing nice lingerie. One day I just put on my soon to be wife’s panties and wore them for the day. It was very occasional after that and then progressed to fully dressing over the following thirty years.
I was 13 and it was my mom’s romantic/bridal lingerie, it was absolute heaven and I was immediately hooked on romantic lingerie from that point forward, to the point where by my late teens I felt so feminine wearing lingerie all of the time that I wanted a boyfriend to wear it to bed for, which happened for me.
I grew up in an atmosphere where boys were expected to be boys. So I did all the macho things right up to my mid 30’s. I was the all outdoor boy, skiing, hiking, rock-climbing, car racing, endurance ski races, ocean sailing. All the while as was doing my macho thing I wanted to be feminine. I hid my desires well. No one knew. I married and then things became problematic. I longed to wear nightgowns and peignoirs. Finally one night I went to bed in a nightgown. My wife, understandably, had a fit. But that was the beginning. So separate rooms were the order. For years i slept in some gorgeous nighties. Oh yes, I also wore a bra and Brest forms. I was in heaven. Then after 50 years of marriage my wife died very suddenly of cancer. After awhile I re-married and my wife of now accepts my need and so I can dress two days per week and I have a lovely wardrobe. I can not go out in public, though I long to do so, However I am thankful that I can wear my clothes on a semi regular basis. I feel I ma blessed. I long to be with ladies like me but, that will never be. Just know I envy those of you who can meet, walk, be seen in public. Love to you all. Katerina.
You never know. My wife was not the least bit accepting, nor did I expect her to be, when she learned of my feminine desires. I thought I would never be able to wear panties, let alone a bra. However, that did change to a surprising level of acceptance. Unfortunately, counselors and friends persuaded her that I was deviant and a mental case, so she deduced I was a sex addict and dangerous to be around. We saw counselors who made light of it, but she insisted I change and found an ignorant counselor who agreed with her. That all led to divorce. Enough time has passed since then that I suspect it would be easier now for one to learn the truth and accept it, and I might yet be married were that true. This topic is now commonplace. It used to be illegal to crossdress and I knew people who were thrown into mental institutions and scheduled for lobotomies. Fortunately, it is easier now for one to get better advice, but you DO have to be careful who you seek out and trust before taking more risk than you can tolerate.
I was either 8 or 9 when I first crossdressed wearing dresses, slips, and panties from my Grand Aunt’s closets and drawers. Although at the time I was just a boy playing dress-up.
I consider my first actual crossdressing experience at almost 46 (2018). I attended my first local CD/TG support group meeting full en fem; wearing a dress, bra, half slip, panty, hosiery, wig, and heels.
The CD/TG support group is called Crossport; located in Cincinnati, OH.
I was doing some internet searches for local “crossdresser support services” in my area and a link came up mentioning a “Pride Fair” at the local VA Hospital and that the Crossport organization was going to have an information booth set up there.
I think I was around 12. I do remember going into my parents room and trying on my moms panties. Then I found and old bikini she had. I had a try that on. I was hooked.
I was 7 and it was my parents who thought it would be cute to dress me like my sister. Everyone thought I was my sister but uh oh. I liked it a lot. It grew from there.
I may have told this story before, so when I was 10 I had a girl friend who was about a year older. She was the wing commander’s daughter at Whiteman AFB. She and I had met when I moved there about 6 months prior. Anyway she and I were very close. It was summer break and very hot so she was playing inside a lot. She liked dressing up and playing with makeup and having tea parties and such. She invited me over and wanted me to dress as a girl to play so I did. We did this for several days and her mother must have thought it was nice. She bought a wig and several dresses for me as well as age appropriate under garments , lacy of course. Swearing me to secrecy I spent the entire summer almost everyday dressing up and playing. She even took us out shopping and to the movies a couple of times. I can’t believe the risk she took for doing this. Sadly they moved shortly after that summer.
It was an unusual and uplifting experience that I cherish to this day
Love
Tommie 💋
As a teenager, there was an older friend of the family that eventually glommed onto me and I näively hung around him. When no-one was at his home over weekends, he invited me there for sleepovers. If I recall correctly, on most of these times, he suggested that I put on a bra and stuffed the cups with socks or something. And, yes, we mutually masturbated each other, but that was about it. This predatory relationship didn’t last all that long and I stopped it, resenting him. Today, this would be called grooming.
The crossdressing part was there, but it didn’t really do anything for me sexually or emotionally, which I am sure was one of his goals. It was only underwear, in bed, and not outer clothes. We just didn’t get there.
I remember that he glommed onto another person in my highschool and, later, he was working his way up in his church administration. He had a short life and I don’t think that he lived much beyond 30-35 or so, probably saving others from him.
So, don’t worry about me. No pitty parties, please. It was not something that ever scarred me, but it was my first, real introduction to crossdressing of a sort. It is what it is.
My first dressing experiences were about age 13. When home alone (not often as I have 2 brothers) I would put on my mom’s bras and girdles. I probably stopped about age 15 when I started dating. I was married to my 1st wife for 17 years. I likely tried on her pantyhose 8 or 10 times over the years. I always was immediately aroused and had to take care of business. I’ve been married to my current wife for 40 years. I started dressing 3 years ago next month. I started with just panties on a daily basis. It didn’t take long and I dress some portion of every day. Do the math and you will figure out I started serious crossdressing at age 74.
It started as a baby because my parents could not afford clothes for me so they dressed me in my older sisters clothes. By 10 I was wearing panties and started wearing my sisters bras soon after. By 15 I was dressing en femme.
I was around eight. I had always been secretly fascinated with dresses, so I flat out asked my mother if I could try one on. And she said yes. So there I was, wearing a dress, in the living room. My two sisters were there with me, and they were also wearing dresses. And I had a ball, twirling around and looking pretty. Three sisters enjoying themselves in their dresses!
I have no recollection of sneaking into Mom’s lingerie drawer at a young age. But for all intents and purposes, in my preadolescent years, I was more little girl than little boy. Enjoyed playing tea and Barbie’s with the neighbor girls. Even asked for a Barbie for Christmas one year. You can imagine my disappointment when I got a GI Joe. Fast forward to the late 80s when I was home alone and discovered a discarded pair of my spouse’s pantyhose in the bathroom trash. Even though they were too small for me, I forced them on and couldn’t believe how incredible they felt! Fast forward to my early 60s (several years ago) and something made me go and get some lingerie. When I put it on, I knew right then and there that women’s clothing was my future and haven’t looked back since.
The family legend is, that as a newborn my older sister started putting me into her old things. Mama thought it was cute and now she did not have to go right out and buy new things for me. As soon as I was out of diapers, I was into her panties too. As far back as I can remember I was always in girl clothes, up untill school and maybe even later.
I was 5 and would often sneak my mom’s lacy bits and pantyhose and dress up in the bathroom. And I got caught, too. Had to have a sitdown conversation about it and was so embarrassed and ashamed I thought I would die. I denied everything except “curiosity” and was much more careful after that! It took decades to sort out that I was born this way…
I must have been 4, maybe 3. My older neighbour (all of 6 years old) sent me home with her panties on after we played doctor. I was really ashamed and can’t recall the interaction with my parents after, but I do recall my main reason for being ashamed was that I enjoyed it.
For many years after, I would dream of my mother offering herself to me. Only she had my dad’s “parts”.
Fast-forward to my first marriage (2009-2013), we were on a rough patch (again), I was home alone and had smoked a joint and eaten some weed, too. I can’t remember being that high before. All of a sudden, during self-gratification, I started picturing myself as a girl. I don’t think the image ever left my mind, because months later I put on a pair of my then-wife’s thongs that she would only wear during intimate times — that specific pair had never been worn (I told you it was a rough patch). And I took pictures of myself. Then I deleted the pictures and never thought of it again.
I got divorced, started seeing a girl, and one night she asked me to strip for her. For whatever reason, I got a pair of her thongs and used that to tie my long hair. After I was done with the drab, I put on her panties and kept on.
A year later, during therapy, I recalled those memories of my “transexual mother” — who was actually me.
I never thought of dressing again until one night a couple of years ago (I was 37 or 38) when I saw myself longing for a pair of my wife’s panties. I needed to wear them. So I waited for her to fall asleep, grabbed the panties from the hamper, and felt so, so calm.
Edit: giving it a second thought, I can’t recall if I started dressing again before or after losing our only daughter. I want to say after. She was stillborn at 39 and a half weeks, and just the week before we had been at the midwife’s and heard her heartbeat. Placental abruption is cruel.
I am surprised at the number of you who can remember anything at such a young age, say, 3-4. I can barely remember anything before, I don’t know, maybe 8. Just a few things: learning to ride a bike, hitting my head hard a couple of times, our home lot, first day of school. Not a lot of things.
Lucky you.
Hi all, Like many on this site, my first memory was around age 4 or 5. I don’t know why, but had the urge to try on my mothers nylon panties in our outside toilet at night, they were way too big and felt very aroused and not knowing what was going on. In early teens, I discovered pantyhose, and have enjoyed them ever since. In more recent years, am finding a strong urge to fully dress and feel ever so more relaxed.
I have spent years trying to understand what it was all about and feeling very isolated in not being able to share my experiences.
I have often thought about this aspect of my crossdressing and, the fact is, I cannot remember a time when I didn’t think about, desire and/or actually dress (to some degree). I suppose the the need and, at least, curiosity started as soon as I began to notice the real differences between boys and girls, especially clothes. So, I suppose, around four years old.
My first real memory of CD/TV/TG activity, though, was when I was probably about six years old. It was getting near Christmas and my two older brothers and I were getting excited about what presents Santa may be bringing us. One night, my eldest brother came into the bedroom to wake up us two younger boys in order to sneek-search our parents’ room in order to find any already bought toys, gifts and goodies! I know I wasn’t really sure about what was going on. When we entered Mum and Dad’s room, I went straight for the wardrobe where my mother’s shiny polyester work uniform dress was hanging on the door. I slid it down from the hanger and slid my little arms into the short sleeves. I remember feeling the cool smooth fabric on my naked back. It was, obviously, far too long for me and I can remember the skirt draping and dragging on the floor as it made and elegant swooshing sound. My two siblings were far too involved in their innocent yet greedy searching to notice my excursion into feminine fantasy. All of a sudden, my father entered the room and quickly sent us back to bed, he seemed to not really notice how I was dressed and more bothered about us leaving as quickly as possible. Nobody mentioned any aspect about that night ever again.
There were some other opportune moments while I was still very young: taking a pleated tartan skirt from the floor of my sisters’ room and slipping into a pair of nude heeled sandals that I saw in their open doorway. Countless returns to my mother’s room a couple of days after I noticed her wearing something new. Finding a lipstick down the side of an armchair then hiding in a shrubbery in the garden to apply it, without the aid of a mirror!
I even remember the first time I had a real dream about crossdressing. I was eight years old and there was a very pretty girl at school called Angela. She was very popular, she had a beautiful smile and always wore very feminine clothes. Sometimes she would come to school in one of two typical pretty 70s dresses. Short puff sleeves, knee length skirt and a psychedelic pattern detail on the front of the bodice. One of these dresses was yellow, one lavender. In that dream, my mother handed me a reddish plastic carrier bag, obviously the type from a clothes store. I quickly took the bag upstairs to the bedroom. In the bag was a copy of Angela’s lavender dress. I put the dress on. I stood in front of the mirror. A pretty girl. I remember thinking “no more wishing”.
As I entered my adolescence, my crossdressing needs and desires were obviously not going away. They took on an erotic nature aswell as staying a relaxing comfort, an innocent excitement and the outside manifestation of my inner identity.
My mother sadly died when I was fourteen. I dressed in her clothes more and more, for emotional comfort and to feel close to her. Her black satin blouse with typically 70s teardrop collar, puff sleeves with long tight three-buttoned cuffs was the focus of my beautiful escapism.
I am almost 57 now, my life has been fraught with emotional and psychological problems. I can trace each one of my difficulties back to my crossdressing, rather my unsatisfied desires, the burden of keeping a secret.
I would not describe myself as gay but I know now that my desire to be/dress as/appear a woman is far greater than my attraction to women.
My first time was when I was a young teenager. My mother would hang her aerobics outfits to dry after washing them in the bathroom I typically used in the house. In the evenings, I would try them on once dry. I’m confident this is where I developed my love for the feeling of one piece swimsuits and tights.
I was in the 3rd grade
Stealing moms and sisters stuff.
Went full-time after a 1999 New Years Eve Party at a dance club.
I wore a black cocktail dress and was drunk off my butt. I was on the dance floor most of the night and I must have danced with ever girl there (at least that what it seemed like) and I even went home with a girl that night.
Been dressing ever since then.
Hippie
I’m surprised I didn’t see this the first time around, maybe because I had mentioned it elsewhere and didn’t want to repeat myself. Now, thinking about it, I’ll cover it again, and add a detail I didn’t cover elsewhere.
I remember the moment quite well, just not the exact year. We moved the summer of my 4th year, same town, bigger house, about 1/2 mile away, and my father died just after that in a terrible accident. I remember that vividly, what I was doing, how I found out, people around me. So, my first remembered expression of my desires was after this, whether it was within the next month or the next summer, I’m not sure, but it was warm out.
Anyway, I asked my mother to make me a dress. I have no idea what her thoughts might have been, but she did, out of kraft paper, and scotch tape I guess. It was a full size dress, although I don’t remember what the length was, or sleeves, or other descriptions. I distinctly remember wearing it outside in our side yard, until it probably ripped. And I remember that I was very happy.
That’s the first full memory I have of wanting to wear female clothing…and probably wishing I were a girl.
My next fully fleshed out memory of this is about 3 years later, same house, finding a Halloween type costume wig, putting it on, and imagining I was a young girl. That would be age 7 or 8.
And here’s the rest of the story of that first memory. At my father’s passing I was the middle child of 3 boys, 6, 4 and newborn. Yes, my younger brother was a month old when his father died. Thinking back on it, and listening to others, well, my older brother was told he was now the ‘man’ of the family. My younger one was an infant and of course, needed feeding and changing. And I suspect that left me to be there for and perhaps provide some kind of solace to my mother…which I suspect she needed badly, and I was more than willing to do what little I could, or knew how.
Did this precipitate my lifelong desires? Did I have thoughts before this? I don’t know, all I know is that the thoughts, desires, emotions all continued on, sometimes stronger, sometimes not as much, but they never went away. And in the years to come, as I matured, so did my ability to begin satisfying in some way those desires, from sneaking items to eventually starting to build my own wardrobe.
Oh, and I do have very fully formed memories from age 3 1/2 at Halloween, with about another maybe 10 or 12 or so leading up to the house move, very fully formed and confirmed by my mother and older brother.
Hugs, ChloëC
I was 14. About the same size as my Mother and older sister. I had longer hair and was often mistaken for a girl. Home alone for the day and tried on so many of their clothes. I liked the way I looked and just posed in the mirror after trying on so many outfits. I was hooked after that and continued to dress up quite often
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It was when I was 9 years old. Wearing my mums and sisters bra and panties.
12 or 13 I think, was home alone and found stockings and a girdle also a bikini my aunt had loaned my mother. Been a lifetime crossdresser since then.
Katie.
with reading a lot of your posts, I noticed that in most of our personal experiences started with what would we done without mom clothes ,Most of us started with trying on are moms clothes I myself was age 9 or 10, did the same panties /bras which of course were really big,LOL, but I put them on anyway because you like the way they felt, then I moved on to wearing my girlfriends underwear when she was not around, and then finally buying my own bra and panties, soft silky, nighties, pantyhose , I believe one of the toughest things as I was growing up and getting into wearing feminine clothes, was keeping everything hidden. in your dresser in your closet, put them out in the garage stuffed in a box and also like wearing a bra around. without anybody noticing the bra lines, i’m sure we all got all those stories. and I love hearing from you all about all of our life experiences, it makes me feel like we’re all in this together .It’s been a long, crazy life. and you know what? I loved every silky, soft, sexy moment that I wore.them,, thank you,❤️🌹
Hi Darlene. An interesting post. Personally I never thought of trying on my mother’s clothes. I had no inkling until in my early twenties when I experienced an overwhelming urge to put on some lipstick and it all just snowballed from there.
But it raises an interesting question. If you ladies had not slipped on your mum’s undies as a child would you still have gone on to become a crossdresser? Is our little kink nature or nurture?
My guess is yes, we would still end up en femme. I don’t know why we do what we do, but we all start at different ages, but there does seem to a well defined spike at puberty, and there I think the reason is obvious. With all the hormones surging, and girls on our mind we seek ways to embrace those feelings and a putting on girl things is one of those. No doubt we found it pleasurable, I certainly did, and had my first orgasm. No wonder I like it so much.
Others started younger, so not a sexual/erotic thing. Another peak seems to be around early twenties, and I suspect it is because that is the first time many of us are having serious relationships beyond the high school flings. There is now a handy source of bras and panties close at hand. Some start later in life, even into their senior years. I think the bottom line is that we often try wearing femme things out of curiosity (often driven by other emotions), and find how nice it feels, and like any pleasurable experience we want to repeat it. To get into brain chemistry, we get a flood of pleasure hormones and want that release again and again.
I sometimes wonder if there are two types of crossdressers…those who are, and those if haven’t tried it yet.
I think you are close to the truth when you say there are only two types of crossdressers… those who are and those who have not tried it yet. I might go further… of those who have tried crossdressing, I suspect most find it enjoyable and continue doing so. If seeing is believing, then trying is doing, and those who DO are apt to never go back.
I went to a service when I first fully dressed, not expecting it to serve more than a weekend. But I was hooked immediately. The lady who dressed me then told me that it’s like squeezing a toothpaste tube. It can never return. I often have wondered what I would have done had she told me this in advance. Still, I believe it would be a service to adolescents to encourage them to try crossdressing so they won’t build a lifetime of expectations that may not materialize. Better to know before cementing marital relationships than to find out later that you cannot stop and your spouse won’t accept or forgive you if you cannot.
It is often said that one should take accountability for any deception,and we should be revealing to a potential life partner before creating an untenable situation. But many of us learn only later in life that we are crossdressers or have any comprehension of what this is or the fact that we cannot change or control it. So the guilt of crossdressing is compounded by the fact that we did not tell a loving partner. But how can we tell what we do not know or understand?? Ignorance is not always bliss.
I started around 14 years old wearing my mother’s things I always felt happy when she was getting the for work walking around in her panties and bras so many gourgous colors I felt that. I wanted to wear bras and panties to so as time went on I started to wear her bras and panties and study how she would do her makeup and put on pretty dresses and pantyhose after dressing for years I got caught on PURPOSE TO SHE CAME HOME EARLY OND TIME and there I was fully dressed in one of her dresses I felt so so happy And she just stood there with a smile on her face and said I finally have a daughter how happy I was to hear that so that was the beginning of my life as a cross dresser years later now mother looking down and saying to me she taught me right on how to be a woman today by the end of the year I can finally transition to the woman I always felt I was and DEFINITELY WANT TO BE DEPENDS ON MY Financial situation but I need to badly hope everyone understands have a beautiful day everyone besafe becareful and stay the girl you love to be
Ambermaria, wow! ” …and there I was fully dressed in one of her dresses . I felt so so happy And she just stood there with a smile on her face and said I finally have a daughter. how happy I was to hear that…” Thank you for sharing your story, your beloved mother’s love for you and yours of her!
Connie🌹
I have been a cross dresser my entire life. At 4-5 I would regularly wear my older sister’s yellow satin and chiffon party dress with white tights and black Mary Jane shoes. I would put on lipstick and eye shadow. I was “caught” by my mother many times. Most of the time I was allowed to wear it until it was time for my Dad to come home from work.
A few years later I would join cub scouts and volunteered for every female role we had in our skits and plays so I could get my mother to help me dress up in costumes I had a few dresses and a couple of wigs at my disposal
When I was around 10-11 I was invited to a Halloween party I begged and begged until J cried in order to convince my mother to buy me a matching bra and panties a new red and white polka dot dress, a new long blonde wig and heels she did my makeup and I was a big hit with my friends and their mothers
I dressed a lot thru Jr High and High School I even dressed as a cheerleader a few times but that is a long story for another time
Needless to say “I enjoy being a girl”
I started school at five years old and was dressing then so I’ll say five years old. The school system back then allowed me in at five, otherwise, I would have had to wait until the following year to start school. My birthday is in November so I really only started two months earlier than allowed back inthe day. No such thing as pre school or kindergarten back then.
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Am born with it
Before age five. It was a costume for a skit my cousins and I made up. Our moms were both divorced and we were all living with our grandparents. I had thoughts of being Wonder Woman, or the Black Cat (Harvey Comics), or Batwoman when reading comics back then, too.
Like some here, it started at birth with hand my downs from my older sister. I use to given her blouses and socks and shoes. I think around 3 or 4 one day I put on a pair of her tights. I didn’t have any clean socks so I natural used those. Didn’t know I wasn’t supposed to. My dad blew his lid and mom never gave me any hand me down after that. Only thing I was given after that was a pair of sisters saddle shoes. This whole time I had been playing with dolls and other girly toys. Most of the kids in the neighborhood were girls my age anyway, so we played house and such.
Other topics I have gone in to further details of my childhood, so I’ll leave it here.I was around 7 or 8. My sister and I were home during the summer. She would dress me up in her clothes and we would go outside and play. The whole summer I would play outside as a girl. We would go swimming and I would wear one of her bathing suits. It all came to a stop when school shopping came around. I asked my mom for girl clothes and she would not buy them and we were told no more playing dress up.
This has been a very long and ongoing thread, so I will contribute.
I was 14 standing in front of my mom’s full length mirror, admiring myself dressed in her green flower pattern cotton house dress. I remember thinking to myself, “this looks right, this feels right.” Eventually I grew out of my mom’s clothes and disappeared deep into the closet. But the stirring of my inner girl, while giving my mom’s wardrobe a workout, never went away.When I was 10, my mom dressed me as a girl for Halloween. She dressed me up in a short skirt, pantyhose, go-go boots (it was the 70’s), tight sweater (with boobs that were way too big), wig, and makeup. Of course I protested vigorously, but secretly I was loving every minute of it. We went out, house to house, walking the neighborhood… it was exhilarating. I was hooked!! It was even better when several of the neighbors didn’t recognize me and commented on what a pretty girl I was (maybe they knew, but I didn’t care because I was loving being complimented as a girl). Again, I was double hooked!! In my mind, I was simply a girl in a go-go dancer costume.
Luv, Cindy
Oh that is lovely Cindy.When I was twelve in 1972 and just starting my crossdressing journey it was my ultimate fantasy to be a go girl with those lovely boots and the tights.It must have been gratifying to get compliments from your neighbours about being a pretty girl.What a wonderful story and great memories.
Cindy,
Out of curiosity, did your mom know that you’d enjoy it? Just seems a slightly odd choice for Halloween of someone that age if she didn’t have some kind of inkling.
Katie
Hi Katie,
Great question. I honestly don’t know why she did it. I’m pretty sure she thought I was miserable. And… we never spoke of it again after that night. Maybe she saw something in me that I couldn’t see myself. I often wonder if she did. If so, I missed the opportunity of a lifetime to have possibly, maybe, perhaps continued dressing with her blessing and help. Alas, I will never know.
Luv, Cindy
I think I was maybe 10. I found a pair of my sister’s nylon panties in the laundry hamper. They didn’t look dirty. And I was fascinated with how the material felt. So I put them on and wore them under my shorts. Then went outside to play as if nothing was different. Of course I knew I was wearing them and that made the whole experience surreal. It was probably two or three hours before I went back inside and changed back into my own underwear. But from that point on I was hooked.
Hi everyone. Great answers.
I seem to be the outlier as it was my early 30s, but had thoughts before that.
My wonderful wife let me try on a few of her things and boy did I take right to it.
However, my wife didn’t really want me to go to far with it, which is understandable and okay as she was the best wife I could have ever asked for.
After she passed I CD for about a year and a half then took a long break.
Okay if anyone remembers records, LOL, not to be a broken record for other posts, but …
CD came back full for me in 2022 and have embraced it completely privately and just love it.
Not having an SO I can dress all the time at home which I enjoy and can explore my cross dressing like buying clothes on-line without having to worry about it.
So, maybe late to the party, but enjoying every day I can dress now and enjoying being a part of CDH where on-line I can be Catherine, talk positively and openly with other cross dressers about my dressing and learn from them.
Catherine
I agree with Lisa that Cindy is a lucky thing! For me, it was age 7 exploring my sister’s wardrobe. I remember getting fully dressed in her underthings, skirt and blouse. I had a blast. I also remember my sister didn’t like it one bit and I had to do an embarrassing fashion show for her and my mom as punishment. What if instead my mom had bought me my own purple flowered playdress?
35. On a lazy Friday night, I was laying on our bed watching TV, while my wife was working with a dress, she had altered from a “zip up” to a “lace up” back. She was trying to thread this one inch ribbon back and forth and was getting aggravated as it kept twisting up on her. She asked if I could, help… without hesitation, I jumped up and tried to help her with the ribbon. She could see what I was doing in the mirror, and told me it was still wrong. She asked if I could just step into it for a minute while, she laced it up, so she could get both hands on and see what she was doing. She assured me, it would only take a minute and she’d be done. I reluctantly agreed, holding it up while she laced me up, I kept my eyes closed and just told myself, “don’t look down, it’ll be over in a minute” But, as I felt the backside closing up as the lace got tighter, the satin material, a sensation came over. I actually liked the way it felt on me. I opened my eyes and looked down…it wasn’t scary like I thought it’d be. It was the same dress, I’d seen hanging in our closet only with a much different view point as I looked down on it. She finished with the lace up back, and instead of just letting it drop off, she actually tied it, and walks around in front of me, smiles and says “wow, it actually fits you really good. Does it feel good?” When she asked me that, I kinda felt like my face must have been a dead giveaway. I was supposed to hate it…but, I didn’t. I didn’t wanna say how much I liked it, but, I didn’t wanna say I hated it either and slam the door on this ever happening again. She told me to check it out in the mirror, I turned and stepped towards the mirror and saw my hairy leg come out from underneath the open front…and just made an awkward joke, and kinda played the middle road…I said “next time, give me a little heads up so I can shave” She smiled and said “definitely”
I know that’s probably, long and detailed, but it wasn’t that long ago. I was 35, and I remember that night vividly, because it changed everything. I’m 43 now.My mom found me, wearing her 💄 when i was 4 , she fixed it for me, told me to go see how pretty i was, and too ask for help next time.
Well a few times. I would watch her put her makeup on and sometimes she would smile and ask if i wanted some. I did. She had me pout. One nite the baby sitter saw me and mom told her i might like to get my nails painted. I did.
Unfortunately not again until i came out as tg when i was 30 something. But at 17 she suggested i was gay and it was ok and i should try dTing guys.
Asking if i wanted some i was 4 or 5, suggesting i try dating a bot was at 17. She suggested one from our club. Then she told him i might be gay and he should talk to me. He did, i did.
I was about 22 at the time bought my first boat. Took it to the beach and plopped down in my beach chair hiked up my shorts exposing as much skin as the law would allow. I got sun burned or should I say sun poisoned so bad. I went to work Monday in so much pain from my male underwear band. When I got home my wife gave me a pair of her panties that sat below the burn area in all areas . That was it the comfort of the panties was more then any pair of mens undies that I started wearing full time. I then began to check other things and loved it. Boring I know but thats how it started!
I think I was around 14 or 15. When my parents took the dog out in the evening I’d disappear upstairs and wear my mother’s nylons and boots. After that, I’d remove nylons, panties and bras from washing lines and wear them too. Eventually I got caught by my mother, came up with a staggeringly crap excuse, dumped the whole lot then started again a few weeks later. Then I got engaged and wore my fiancee’s stuff…….the story goes on and on.
I’ve been dressing regularly in the last few months and a potential partner wants me to do more…….not a terrible place to be.
I reckon I was about 14. I found a tweed pencil skirt that my mum had clearly grown out of and was stored in the bottom of the spare wardrobe in my room. It fitted me perfectly and had a slit at the back and a silky lining. I used to put I on in bed once I knew everyone else was asleep and hope I didn’t fall asleep with it on!!
I was 10 and I wanted to try on a beautiful dress that my younger sister had hanging in her closet.
The problem 2was that she was a lot smaller than me. I put my arms into the dress and was able to get it down to my waist but couldn’t button it up. Even so, I saw a wonderful image of a girl in the mirror. It was a beautiful experience.I would have been about 4 I was in my older sister’s room, she’s 5yrs older and found a pretty yellow dress, think Disney princess, and tried it on. Bad idea. I managed to get on but then heard someone come inside and in my rush to get it off got stuck in it as my mum came into the room. I don’t remember the consequences but I never tried on anything to small on again. Everything was loose fitting from then unless I knew I had plenty of time. After talking to my sister about a few years ago I found out she was not happy because I ripped it and it had to be thrown out. She had wanted to save it because it was the dress she wore for Queen Elizabeth’s visit in 1977, the year I was born.
I was around 7 or 8. For whatever reason I found myself in my parents bedroom going through mums underwear drawer. I put a bra and panties on and it felt amazing as I posed in front of her full length mirror.
I’ve been doing it ever since on and off up until about a year ago when my 3rd (and final) wife encouraged me to do whatever makes me happy. I’ve been shaving everywhere since then too.
I haven’t gone as far as wigs or makeup, I’m not sure I want to just yet. But I love lingerie and have recently been buying dresses. Venturing outside is a massive thrill…when I pluck up the courage!
Steph x
I was about 12. I had 3 brothers, no sisters. My curiosity was peaked when I saw a porn magazine at a neighbors house when I went across the street to feed their dog or babysit. There was an ad in one magazine for another magazine and the pic was a guy in a bikini. I don’t remember which happened first after that – either I started looking through my mother’s things in her bedroom or I found an old bikini of hers in our storage room. That’s where it started and I’ve been hooked ever since.
Fiona-Ann, You say this is an “easy one”, yet it is one of the most fundamental, important questions I have seen asked on this site. When do we become who we are and is this evidenced by our earliest encounters or is there more to it? Are we born this way? Can we alter, understand, or conrol it? Do we even know what “it” is? I have spent all day reading and pondering the responses.
I plan to attend an Eddie/Susie Izzard event soon… an opportunity to dress up AND learn from a recognized expert on the subject (if there IS such a thing). If any plan to be in Atlanta September 9, please PM me and join me for a CD holiday.
Izzard (who believes she is “gender fluid) believes the day will come when we have scientific proof that this is genetic. While I believe there is an element of both nature and nurture, there is a lot of evidence pointing toward the conclusion that we indeed ARE born this way, and there is only so much we can change. I believe nurture plays a role in helping us become who we are.. the stories told in this amplify this belief.. acceptance of family and peers, for instance, can greatly influence our paths. Still, who we are seems largely outside our control. I have yet to meet a crossdresser who can successfully repress their femininity any more than Aladdin could put the genie back in the bottle.
Tangentially, I believe there is a difference between someone who is a “woman” vs. one who merely has a need to express innate feminine characteristics. I think such characteristics exist in everyone… there is just a difference in degree. The great majority of those in the former group have a strong awareness of being a woman from their earliest memories and are more apt to transition. The great majority of the latter become aware of this in their early teens, although in a significant number of cases they may not be presented with the circumstances that lead them to this discovery until much later on. In my case it does not mean it did not exist from youth or even birth… I knew from the time I first pulled Mom’s bra from the hamper circa age 13 that I could not resist its allure, but refused to believe that was permanent. Until age 60 I did not know I was not alone, as I had never known or met another crossdresser so incorrectly thought I could change or control what I could not.
These are just my observations. They lack the level of scientific proof that would convince most researchers.I hope to change this. I have reviewed and conducted demographic surveys and a significant amount of literature on the subject and served as an outreach director for nearly a decade, having opportunity to interview hundreds of crossdressers, becoming convinced that this is far more than a hunch. Going further, I have compiled statistics and used these in classroom presentations, outreach to diversity directors, students, educators, and the transgender community, discovering that what most believe true frequently contradicts the underlying data I have gathered from crossdressers themselves who seek support and knowledge.
I constructed a simple multiple choice test based upon data gathered from hundreds of crossdressers I have interviewed, all seeking to join a support group of their peers.. 11 questions for which I believed answers to be objective and not difficult. I have given this to hundreds, if not thousands of students, educators and transgender individuals. I initially expected most would respond correctly to every question. The survey questions and answers closely match another survey I unearthed by a prominent crossdresser/blogger. Yet no one yet has answered all questions correctly. Even random guessing generates answers which are more accurate than many groups polled.
My original object was to educate others as to who we are in hopes of gaining broader understanding, acceptance, and advocacy. But I have concluded that this is not “an easy one”. I have modified that objective to simply help people understand that the facts are not as simple as one might think. Knowing that, we should be cautious about advocating points of view that can work their way into law and dangerous practices without making it clear that much of what we believe true is very apt to prove false. At the very least, we need to recognize that there are fundamental differences between subsets of people. This is evident from responses to this very revealing question.
This is a long way of saying I agree with Katie that there are elements of both nature and nurture and I think this question, far from being an “easy one”, is an excellent, illuminating one, well deserving of the wealth of responses received.
Pardon my long response, but you have struck gold, in my opinion. It is worth mining this one.
Hi Fiona,
I was eleven years old when I tried my sisters dress on. I can’t describe the feeling I had when I pulled it over my head. Once I had it settled in place, I just stood there looking down at myself.
Dear Fiona Anne,
At the young age of size I tried on my mothers lingerie and several garments. I vividly remember fiddling with the front clasp of the bra, adjusting the straps; Feeling the girdle tightening around my waist. Trying on a dress and adjusting the zippers.
The fascinating part i feel was my lack of a desire to look in the mirror dressed. I began to feel as sense of “complete” just putting on the garments. The magic and glamor has not faded since the first time
A spark which started a long bright burning flame.
With reminiscence and gratitude,
The Bluest Belladonna
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