What prompted you to start crossdressing?

[Tabitha_Sinn]

The truth is, I really don't remember what prompted me to start crossdressing, but what was the case with you? (if you remember!)

[Jenn A116]

I can't point to any particular event or trigger. I can just recall even as a young child of 6 that I wished I could dress like the girls. Never wanted to actually be a girl, but just to dress like one.

[Kate Simmons]

Nothing prompted me per se. I just started doing it and it felt right some 57 years ago. :battingeyelashes::)

[Fiona123]

Curiosity. I recall being 8 or 10 yrs old and trying on a discarded one piece swimsuit one of my sisters wore. Been hooked ever since.🌺

[JeanTG]

My mother.

[Tina_gm]

I was in a bar. I was 17 years old. I saw a girl who I found to be attractive. Suddenly I felt a sense of wanting to BE her, rather than be with her.

[Mykaa]

thats a good question, my oldest memories of it are probly around 4 or 5, what makes a 4 or 5 year old do that?

[Virginia1983]

I completely understand. I size women up - their makeup, nails, clothes, heels, everything - and want to be them and have their boyfriends/husbands!

[JennyToday]

I have a pretty specific memory of the first time. I'm not sure the exact age, but something like 11 or 12. I got up in the middle of the night to use the bathroom and a pair of my mom's panties were sitting out. I was curious and decided to try them on.

I often wonder would any of this have started if not for that moment? Or was I destined to come around to it sooner or later?

[Jenniferathome]

I was born a cross dresser. Opportunity is what prompted me.

[Robin777]

For me, I was attracted to women's clothing when I was real young not realizing why. I remember trying on my mothers shoes. I was always attracted to the female clothing in the Sears and Penny's catalogs. I remember pestering my mom for a boy's nightshirt(which I got) which was like a nightgown. When I hit puberty and the hormones kicked in, I started with women's underwear and it went from there because it felt like the natural thing to do.

[Virginia1983]

Yep- loved to dress in her lingerie and clothes - lipstick and everything. Completely fascinated with reading my mothers Cosmopolitan and Playgirl magazines - and romance novels - in my teens.

[SeanErin]

For some reason I put on a pair of hot pink satiny panties ang the gates opened.

[marlacd]

I'd say I'd always wanted to dress. I always admired them, and wanted to be just like them.

[BLUE ORCHID]

Hi Tabatha :hugs:, I'm 73 and I've been in this program for almost 69yrs. ,

I guess at the time it just seamed like a good idea...:daydreaming:...

[Tabitha_Sinn]

Hi BLUE!

Wow! Long time! Only 24 years for me. I am glad I found this site because I have often felt like I was getting older now and often wondered how much longer I would still enjoy dressing. But there are many members here a bit older than me that give me hope that I will still be able to enjoy dressing for many more years to come :-)

[Desiree2bababe]

The feel of Mother's slips, hose, and heels.

[lingerieLiz]

My mother gave me panties to wear when I was 5.

[Terry V]

As a young boy I always envy the girls and what they wore little dresses with pettiecoats and MaryJane shoes, one day my aunt noted how I watched them and asked me if I wanted to try one her friends daughters dresses on of course I said no but the next day she asked me again and I said yes I did and have been dressing ever since, I now thank my aunt for the many times I dress and the felling of freedom it gives me.

[Tabitha_Sinn]

That's so cool, Terry!

[franlee]

The feel and look of the Women's cloths back in 1970. Never thought about dressing in them until after a fixed bet, it seems that it backfired and the results lasted from that first occasion. It is more of a fetish but one I have endeared and use to my advantage. And it is not confusing I enjoyed it and still do and expect to as long as I possibly can.

[mary simpson]

for me it was trying on mom's high heels , i was hooked after that :)

[NewBrendaLee]

Its a big part of who I am. I just wish that I could dress more

[prene]

For me it just seemed right.

Always wanted feminine clothes.

[sandyb40c]

I can't remember any single event, but I remember little bits and pieces of when I was 6 or 7 and having to try on a skirt or dress and sneaking off to the bathroom and trying on things from the laundry basket. This urge never went away and I bought my first bra at 14, after trying on several of my cousin's bras and realizing how right it felt. Now that I'm 50 it is just who I am.

[binair10]

With me it just happened. I do not know how to explain it. If anyone knows the true answer why, please let me know. It has been bugging me for well over 60 years.

Julie.

[JenniferMBlack]

When I was in the fourth fifth and sixth grades nearly every girl was wearing skirts all the time it made me wonder what it was like to wear a skirt. In the seventh grade had the opportunity to try one on. I did and as they say the rest is history.

[Michala]

Hard to say, it's been a long time ago. Don't remember the exact age but it must have been when I was somewhere about the age of 12 that I first tried on my mom's bra. I had gyneomastia at a young age and wondered how my breasts would feel or look in a bra. Liked the feeling of wearing a bra and that grew to wearing more of my mom's clothes. Felt guilty and thought I was the only guy who had ever done that and did it off and on for many years. As I got older it became more common and comfortable. Less of a sexual reason and more of wanting to look like the average woman instead of the hooker look. It certainly wasn't any one thing like someone dressing me up as a girl or being treated like a girl. For me it's more of just "who I am" and no real reason.

[bridget thronton]

I am not sure - i recall being fascinated by wearing girls clothing from a very early age (at age 13 I tried wearing my mother's clothing several times)

[Colo Deb]

When I was 7 or 8 (late 50's), my sister, brother, and I would play dress-up in an old house on the farm. The clothes happened to be dresses. As a teenager, I remember trying on my mother's bra and some other clothes. Many years past by, got married, found a bra my wife discarded, put it on. Then along came the internet and I came across this site. Before long, I started purchasing bras, underwear, then dresses, a wig--it kind of snowballed.

[Alexa CD]

I guess I was intrigued because it was different. I can remember being mistaken for a girl at least twice when I was between about seven and nine, it was probably because of my hair. I think it prompted me to be a little more interested in looking and dressing like a girl, I liked the thought of it and it only grew my already existing thoughts and feelings.

[sara66]

I don't remember what started it. I do remember trying on mom's bra & girdle when is was around 5 and getting caught in my sister's panties when I was 9ish. I suspect but, don't remember, my cousins may have dressed my up when I was little. We spent a lot of time with them.
Sara

[Jennie2]

A light blue cotton short nightie, I just had to try it on, when I was about 8 or 9, progressed from there.

[Rosemary+]

As the lady Gaga song goes "I was born this way", when I was preschool age and that floral sundress that my mother had hanging in her wardrobe, well that dress, for some unknown reason was screaming out to me, saying put me on, wear me,and I I do remember not being able to resist the urge to put it on.
And this is one of my earliest memories,
So I really think it is a case of born this way
Love Rosie

[Crissy Kay]

For me it is one word, and that word is Petticoats, LOL!!!!

[AllisonS]

I know what Dana Carvey as the Church Lady would say... LOL Seriously, I don't know. Hormones? I Dream of Jeannie? A gene I got from my great-grandmother? The immediate prompt, as Jenn said, was the opportunity, at about 13 years old, at my friends house. Big house, lots of sisters.

[Tabitha_Sinn]

for me it was trying on mom's high heels , i was hooked after that :)

mary, I can relate. High heels are the one thing I can't do without! Also, the very first female item I ever purchased. White heels happen to be my favorite color! You have very good taste :-)

[Mollyanne]

I wanted to feel how stockings felt on my legs, how panties felt around my "parts" and how a bra felt around my chest. Now I know how all these things feel and I LIKE IT, I LIKE IT VERY MUCH!!!!!

Molly

[Diedre]

I was around 12. My mother used me as a dress form for sewing alterations. At first I hated it, but then something clicked and I was hooked.

[Katiegirl66]

Around 12 . My sister was a cheerleader and i got the courage to try on her uniform. The feeling was so sexy. From there I went to her panty drawer and was hooked

[Vicky Peters]

I know the exact event but not how old I was at the time. My aunt walked in to my bedroom to ask a question, she was wearing a robe but under that robe was a long line bra , a side zip OBG and stockings. Still leaves an impression in my mind today.

[Patrica Gil]

Seeing an aunt in a pretty beige skirt suit with matching pumps, and nylons. She looked so nice I just had to try it. Loved it and still do wear skirt suits with pumps, and nylons to this day.

[Lily Catherine]

I was curious about how a long, silky skirt felt, so I wore the entire ensemble and loved it. I began presenting as a woman for the sake of it (not acting or whatever) a few years later. Not so much to wear the clothes than... All I can say is that I felt natural looking like that.

[Jennifer_Ph]

L'eggs, Sheer Energy, Sheer To Waist, Suntan, in a silver egg.

[ChloeCleveland]

As a child of the swinging sixties, my mom always had a collection of fantastic wigs and mod dresses and boots. She was stunning then (still is today!), and an inspiration for me. As far back as I remember, I was trying on her wigs, wrapping myself in her scarves, etc. Her style made a real impact on me. Though I repressed those desires as I grew up, I embraced them as an adult when I realized that there was nothing wrong with having an inner sense of female style.

[Emma or Darren]

My first time I was about 15 whilst babysitting for my Dads female friends its happened a hand full of times in the last 30 years including trying my wifes clothes on until amonth ago when the pink mist has come on strong told my SO last weekend giving it time but feel shes brushed it under the carpet so to speak.

[Teri Ray]

Moms bras and panties were too much of an attraction. Saw them and was drawn to try them. Been hooked on female attire ever since. That is the "what" prompted me. The "why" is still the great question.

[Confucius]

What prompted me to start crossdressing? I suppose I just wanted my mother's love.

My mother wanted a daughter when I was born. I was a disappointment. When I was six months old she found herself pregnant again. This time my mother got the daughter she always wanted. My sister was my mother's pampered princess. She was my mother's greatest treasure. I grew up believing that girls were better than boys, and all mothers (and fathers) favored girls. Girls were praised for their appearance, and they all the shiny, glittery things. I was so jealous. So when I was three years old, I started raiding my mom's closet. I would tell my mother that I was just playing "mommy". This would upset her, but I still continued for a couple years. Then by the time I was starting school I was being punished for raiding my mom's clothing.

[Devi SM]

I don't know exactly but my early memories put me behind my parents bedroom door wearing high stockings from my mom and I was masturbating.
I'm sure I was under 9 years old because we moved out that house at my 9th birthday.
The other think I recall that triggers my sexuality very early was that my teacher in elementary, may be second grade found a drawing in my notebooks of a penne and an ass in sexual position for penetration that I draw.. Where I learned that? Why I did draw it? I don't know, But my sexuality and bisexuality began very early, before 7 or 9 years old, then the opportunities to dress my sister's panties, bra just feed the ideas in my mind...

[ClosetED]

Many young boys try on feminine clothing. The real question is why did we continue and they did not? They do it once for curiosity and get no joy out of it and never remember it again. We did get enjoyment and that is what makes us different. Why we got that kind of reinforcement is the real big question - genetics and/or environmental things that may have occurred before we could lay down permannent memories so there is no way for us to now remember.
Hugs, Ellen

[Diane1950]

The first thing I ever did was try on one of mom's one piece swimsuits with its built-in bra cups when I was 12. That's all it took to get me hooked. i'm 66 now, and I've enjoyed every minute.

[budlinda2]

My older sister put makeup and lipstick on me and then later dress me many times, i was 7 and she was 14...I first had a lipstick fetish, then it evolved into crossdressing

[Stacy Lyn]

Had to be my Mom's stockings hanging off the shower curtain and her lipsick on the counter, i was about 8 or 9 atvthe time.

[Charlessa]

while maybe 7 or 8, I tried my sisters panties and loved them. but I didn't get into any other clothes for whatever reason. a couple years ago I finally bought a bra and fell in love! then I decided to try dresses and skirts. why didn't I do this a long time ago? because I love them! I had wanted to try these things but didn't. now I do and I go in public sometimes

[Megan.]

not sure really i just found female clothing so much more comfortable and relaxing

[Lacey New]

This is the question that has always plagued me. Yes, I tried on Mom's and Sister's panties when I was young - probably 13 or 14 and it was quite taboo and exciting as well. And instead of "growing out of it" I guess, for lack of a better term - I became addicted to panties, then additional lingerie, bras, stockings, slips, etc. Later, wanted to do more and complete the look with outerwear. I thought it would end when I got married, but no, the addiction is still there. It is still exciting because the opportunities to fully dress are so rare. So, who knows? Perhaps Ellen is on to something that sets us CDs apart from the young boys who have tried on a pair of panties and then forgotten all about it.
Many young boys try on feminine clothing. The real question is why did we continue and they did not? They do it once for curiosity and get no joy out of it and never remember it again. We did get enjoyment and that is what makes us different. Why we got that kind of reinforcement is the real big question - genetics and/or environmental things that may have occurred before we could lay down permannent memories so there is no way for us to now remember.
Hugs, Ellen

[sometimes_miss]

Short version: Someone wanted to molest me, so he came up with a reason why maybe god made a mistake and I was really supposed to be a girl. He gave me some girls clothes to try on, and, when they fit, declared that he was right. Long version in my bio, link in sig.

[brittdoll]

Bugs Bunny! When I first saw him crossdressed, I could see the fun he was having in all his feminine finery. I needed to try it out for myself and now its part of who I am.

[wanda66]

No big deal one day I had no clean underwear so I bought a pair of moms never thought much about what I was doing. Over time it just became the thing to do. My mom question me On occasion asking me if I have worn them she made a big production out of it so I never thought about it being wrong. Later in life look into other articles of clothing ,I do enjoy wearing skirts. butt that wasn't something a young man dead back in those days. I really have no desire to be a woman. Today at the age of 70 dressing is a activity that I look forward to and address wholeheartedly I thoroughly enjoyed being me weather I am perceived as a woman or a man makes no difference as long as I look presentable and I'm reasonably attractive

[Keely]

thats a good question, my oldest memories of it are probly around 4 or 5, what makes a 4 or 5 year old do that?

Exactly! Been hooked since, 60 years now.

[Girl]

Just always had an overwhelming desire to look like and be a girl, for as long as I can remember.

[CONSUELO]

My older sisters dressed me in a long line open=bottomed girdle for a lark. I was very young, perhaps only five years old or so.
I thought it was a wonderful feeling and my sexual exploration from then on centered on dressing as much as I could.

[MissVirginia-Mae]

I always was fascinated with watching my grandmother in her open bottom girdles and full slips and stockings and this led to exploring her drawers and my mom's drawers.
Dressing started very early with me....
I can still remember dressing up in my grandmothers girdle, stockings and slip and having her right downstairs in the house unknowing and watching thru the window into the backyard so i could
get everything off in time as my sister walked home from school (could see her from afar from that window)

[macada10]

As a teenager, I was supposed to work on an event as stweard, but eventually I had to work as a stwardess due to the uniforms availability and strict dress codes. My female workmates on the event provided a lot support and helped me to dress with enough female dignity....I had a great night with they both then...hooked since then.

[Jannis]

I recall that about 7 or 8 years old, I had the very best feeling by trying on my mother's slips and nightgowns. Every time she would go out and leave me alone in the house, I would put her things on. My curiosity began to build about bras, girdles stockings and panties. By the time I was a teenager, I would dress up fully with Mom's clothes and her breast enhancers including stockings, heels and skirt and sweater. I would walk all over the neighborhood at night. I know people saw me, but no one ever said anything. I was scared once when a car with two middle aged men pulled over to the side of the road and tried to pick me up, thinking I was a girl out at night alone. I did not dress again until several years later. Now I go out dressed regularly to many places such as hair salon, nail salon, grocery store and bank. I am always underdressed at this stage of my life and my hair has grown below my shoulders and frequently gets me addressed as Ma'am even in drab mode. I really feel I could transition but too many family members depend on me to be their "rock." I do get some people telling me to cut my hair or wear less femme footwear, etc. but I dismiss them by saying This is how I like to look. I still escalate my going out in public to more places and wearing more femme or, at least, androgynous clothes. Life goes on.
P

[Patty Phose]

I began wearing stockings and pantyhose at age 4. I don't recall dabbling in other clothing items. It was pretty much pantyhose every day and once in a while stockings. At 17 at the urging of an ex girlfriend, I wore pantyhose out openly with shorts. I was so nervous about getting noticed but much to my surprise no one seemed to.

Men's shorts were shorter back then but I wanted them shorter. I wanted to show off more of my legs. I bought some girls jeans type shorts which were shorter. They were a different fit but I liked them better.

I used to go out to dressed in my shorts and pantyhose to shop for and buy more pantyhose. One day while on a cashier line waiting to buy many pairs of pantyhose, a girl noticed what I was wearing and buying. We got to talking. She wondered why I didn't wear any other feminine clothes. She began buying me some lingerie to try. It was OK and she got a kick out of it so I wore it for her.

Then she thought I should go dressed up as a girl for a Halloween party at her college. She would go as the guy and I would go as the girl. I was reluctant but she reminded me that I would be wearing pantyhose and showing off my legs. That seemed exciting and appealed to me. Out we went buying, some dresses, heels, panties, bras, wigs and makeup. We chose a dress I liked best. It felt natural and comfortable in it. We chose a wig we thought looked best. She helped me with the make up. The heels were awful. I could barely stand in them, let alone walk. When I saw how much sexier they made my legs look, I knew I had to wear them. I wore them in the house everyday and went out walking in them at night. In a couple of weeks I was totally comfortable in them.

I was anxious the night of the party. I nearly changed my mind. Walking from the car to the building was scary not knowing who I might run into and what there reaction would be. No problems there. Then getting inside I worried about the same thing. When I walked into the room it seemed all eyes were on me. Girls were entranced with my look and clothes. I got lot's of compliments. Guys seemed to be intrigued, confused and embarrassed. It's like they wanted to hit on me but knew I wasn't a genetic girl or they were just nervous about approaching a girl they didn't know. I was familiar with the guys side of this encounter but now I was experiencing girl power. It was an amazing night and so much more fun then I could have imagined.

That night, we won "best couple costume". I won "sexiest costume" and "best legs". To top it all off, I met other guys dressed fem who dressed often and had dress up parties. I got invited to join them. So I went from a 4 year old kind playing with stockings to an 18 year old cross dresser and that was just the beginning.

[njcddresser]

Great question and one I've tried to answer for some time. I don't recall any one thing as a child, but when I think back on my childhood there was definitely an attraction to women's things.

Wore panties when I could through my teen years and adulthood. Finally accepted that this is who I am 2 1/2 years ago, told my wife (she accepted this side of me) and since then I've been on a journey of self discovery.

I've learned that I have a very strong feminine side of my personality. Definitely more than just a guy who likes wearing women's clothes, but no plans to present as a woman full time or transition.

[jacques]

hello,
well, when I was young and learning to read I had books about Robin Hood and the Kings & Queens of England... all those heroic men worn colourful tights and I had to wear boring shorts and grey knee socks... so I tried on my sister's tights!
luv J

[Alice_2014_B]

Initially it was high heels.
:)

[Kelly63]

I am pretty sure it was pantyhose!

[sabrinaedwards]

Even in the first grade, I remember the girls in my class wearing Mary Janes and cute dresses. I so wanted to wear them. I think we were born that way, because at least for me I cannot remember a trigger to start these feeling of crossdressing. As I respond now, I am totally feminine in appearance.
Love, Sabrina

[Bobbi46]

Casual thoughts over the years and a strong liking for lingerie then after 2 failed marriages it all reared up and I realised that this is where I need to be amongst my like minded friends. That is what prompted me to dress as to the why I think it is because deep down we all have a feminine side resting there but for us it is no longer resting but being the lovely here and now that we enjoy.

[CatchQueen]

I've been very femme all my life...used to get teased a lot about it too...Wearing women's/girls' clothes and the need to feel/be pretty always came natural to me...

[Alice Torn]

A farm girl who rode my school bus, for six years, with great legs, and wore nice dresses, and Sears and Penneys catologs.

[Joanne108]

Curiosity. I don't remember if it was a dare or I just grabbed a bra from the laundry and tired it on. The bottom line is I enjoyed doing so and have cross dressed ever since.

[LeotardMan]

When, I was younger (5-6yo) I did exercise videos with my Mom as time progressed and I remember wanting to look like her and the ladies on the videos. When, I was 11yo I came home from school and Mom was at work, and I decided to try on one of her leotards and doing a Jane Fonda video and I was hooked!! I moved on to trying on her bras, panties, swimsuits, tights, and pantyhose.

For the most part I just dress when I workout, but sometimes I Just need to be girly!!

Geoff

[Confucius]

I understand that the middle child is more likely to have a low self-esteem, be introverted, and envious. Middle children often believe that they have been left out and struggle for their parent's affection. My sister was the baby in the family and was born one year after myself. She was my mother's pampered little princess, and I grew up believing that my mother would love me more if I was born a girl.

Oh and according to one study, the middle child is more likely to be more sexually adventurous. Well, I was a typical middle child.

[Emma or Darren]

When I was about 6 I remember we were visiting friends of my parents and it was getting late my brother and I were put to bed in the friends bed there was a beautiful dress hanging on the bedroom door and I got to thinking what it would be like to be a girl .
Then from teenage to a few months ago the idea of putting femme clothes on I seem to of mistook as a fetish. Then as I said a couple of months ago I saw a pair of faux leather pants in a store and had this overwhelming urge to buy them so after about 3 visits to the store (gaining courage ) I did so but on wearing them realised how girly I felt since then I cat get enough Ã*nd cant get it out of my head ( just learning to accept its who I am) have since bought panties which I often wear dailyand have grown my nails a bit longer than normal and shave n moisturise which I never used to do. have and am studying women to the enth degree obsessed you might say in fact to the point if I had the option to wake up female I think I would.
.

[Teresa]

Tabitha,
I have never recounted my full story of how my CDing started , this is not the first time this question has been asked but again no one has recalled the same circumstances as mine and the associated dreams . I'm not claiming to be unique I would prefer someone to tell me the same situation occurred with them . I prefer not to tell it in this section but can only see the TS section as a suitable alternative. Yes it was a long time ago but I've lived with the feelings every day since then.

[Elizabeth G]

When I was about 12 or so and developing an interest in girls the only things around the house of visual interest were the Sears and Penney's catalogs. After a while I realized I was just as fascinated by what the models were wearing as I was with the models themselves. It just grew from there.

[suchacutie]

My wife was arranging her ligerie drawer, finding things that didn't fit. We started joking around and since I had lost weight some of those items looked like they would fit me, but after modeling them we joked I needed stockings and heels to finish the look. She laughed, "do it." I bought 6" heels and opaque stockings (they were my avatar early on) and the day I "got dressed" my wife said "wow, look at those legs, we need to buy you a dress." After half an hour she wondered why I was so comfortable dressed as I was since I don't even like costumes at Halloween. That started the conversation, we named my feminine self Tina and started a life for her, now that we understood she existed!

[NancySue]

Definitely pantyhose. When I was 7 or 8, our next door neighbors had two daughters who played "dress up". They asked me to join them. I tried on several things, thinking...yes..they're nice. But when I put hose on, I experience a warm feeling I'd never experienced before. Now I enjoy nylon stockings, panty hose and thigh highs. Couldn't wait to play "dress up" again. 👠👗. Later, they put makeup on me. I loved it. I've been dressing completely for the past couple years. My wonderful wife helps me.

[TakaraYu]

What made me start? Couldn't tell you. I just started doing so one day, however I don't see clothing as having a gender(clothing are just pieces of fabric to be worn) so that might have been why

[CherylFlint]

I’ve come to think of the urge to dress is my “Salmon Spawning Genes� taking control.
And that’s the point, isn’t it? It’s not like a choice.
For those who fight the urge it’s a curse, but for those of us who accept it as a fact-of-life, the art of dressing can be quite fun and relaxing, at least it is for me.
Enjoy Enjoy Enjoy is my suggestion, after all, it’s who you are whether you like it or not, so you might as well like it and have fun with it.

[CatchQueen]

I honestly have no idea...I've dressed since I was in kindergarten and I have always been attracted to tight/sheer/shiny/glam clothes...I just liked them...well before I even knew they were specifically "female" clothes.

[Cristy2]

I'm not one hundred percent sure myself. It is hard to explain where it makes any sense. My biggest encouragement was Christinac when she was still alive. We served together in the Air Force and were very close friends right up to the day she died.

[HollyGreene]

I remember when I was 4 or 5 years old, of all the kids in my street, they were all boys. Then one day a new family moved in and they had a little girl. Probably the first time I'd really met a girl. I remember thinking she was so pretty, and I loved her dress so much I wished I had been a girl.
That memory stayed with me, and I guess many years later when I had a sister, I got the opportunity to try on some of her clothes, and I was hooked.

[Amari]

I was 11 years old. One evening after getting out of the shower I noticed Mum's new bikini knickers in the dirty clothes basket. This was 1969 and bikini and bright colourful underwear (male & female) were new on the market. On impulse I wanted to feel what they were like to wear, I'd not even thought about such a thing before. Arousal was immediate and soon experienced my first orgasm; I didn't know what it was at the time, but I knew I wanted to do it again! Decades later I have more than sufficient female clothing of all types. Wife knows, but doesn't want talk about it or see me in skirts/dresses. She does accept my androgynous dressing - more fem at home, to a lesser degree when out.

[irene9999]

When I was like 6 I looked at my mom's dress and tried it on but of course it was too big. Then in my teens I would try the odd piece of clothing from my sister or my mom (no full dressing tho), I was also fascinated with crossdressers and TG girls anytime I'd see them on TV. It wasn't until my late 20s that I got the urge to fully dress and ever since I've been hooked!

[Janine cd]

I remember trying on my mom's heels when I was about 5 or 6. I also remember being jealous of my younger sister because she got a rabbit fur coat, hat, and muff for Christmas that year and I got an army coat and cap. I really became a crossdresser at about age 10 when I explored my mom's wardrobe. The feel of wearing a slip, panties and bra set me on a life long quest to be feminine.

[Beauty Parlor Bev]

My story is a little different than most, it started with the retirement of my Barber when I was in 3rd grade! I have some memories before that but nothing really solid, although the mention of the JCPennies and Sears catalog bring back visions of the undergarment pages! Anyway, my regular Barber retired and my Mom took me to the "other" Barber in our town. He was much more clipper happy than my normal one and he basically shaved me bald! I was ridiculed at school and can remember my teacher trying to console me. After that traumatic experience, my Mom ended up taking me to her Beautician once my hair finally grew back and eventually it led to me having perms and roller sets at her salon. These were not done to "feminize" me (it was the 70's and male perms were in!) but it ultimately did and here I am today! The Beauty Shop is still my favorite place and I have been enjoying them ever since!263291

[Ceera]

I remember trying on a few of my mom's clothes in the 1960's, when I was less than ten, but it was more curiosity than anything else. I didn't try to keep/hide anything or to wear any of it for more than a few minutes, in the privacy of the basement laundry room. I also tried playing with mom's lipstick in the privacy of my bathroom, but I never tried to wear any makeup when anyone else might see me. My only sister was five years younger than I, so her clothes never would have fit me, and I ignored them.

(Bev, I also recall my mom taking me to a beauty parlor for my haircuts, while I was still less than 12 or so. she went once a month to get her own hair done, and took me with her.)

Had my first gay experience when I was 13 or so. Nothing to do with cross dressing. It kind of scared me, because I knew my dad was homophobic and wouldn't accept me not being straight. I severely repressed any non-straight urges. I knew I was bisexual, but I didn't act on it or explore exactly how I felt.

In 1976 or so, when I was in the Navy after high school and before college, I learned to play "Dungeons and Dragons". For some reason about half of the characters I created to play with were female, and I likes playing them as realistically as I could. For example, when returning from a dungeon raid, while most of the guys headed for the potions shops or weapon shops or a tavern, my first priority was a healer and a good bath, and shopping for a variety of things including new clothes.

1983, married at age 26, and I tried to 'be straight'. Wife knew I was bi but willing to remain straight and monogamous.

Late 1992 - I'm 35 or so. I got Usenet and Internet access via work. Discovered Usenet newsgroups that had a lot of kinky on-line porn. I read a lot about cross dressing, gender swapping, and other topics that in some ways touched on the transgender spectrum, although I didn't self-identify as anything other than a bisexual male. I got active on several Usenet newsgroups that had a certain amount of role playing, and started writing fiction stories. Most of my characters were female.

May 2002, I was 45 or so. Started doing extensive on-line roleplaying as a very detailed female character, and most of the people I played with believed that she was being played by a genetic girl. I found I really liked presenting myself as a female in those on-line venues, but at the time though that would be impossible for me in a face-to-face setting in the 'real world'.

Sept 2005, I got active in a decidedly adult-oriented on-line roleplying venue, where you could see and dress up your characters in a 3D world. I guess you could say I was 'virtually cross-dressing' at that point, because I detailed every aspect of my female characters, right down to their hairstyles and lingerie.

Feb 2010 - I started writing a porn novel and posting it to an on-line forum. Several of the characters eventually experiment with cross dressing. I guess I started to realize that I really wanted to wear women's clothes myself in rel life about a year later, but I didn't act on it.

Mid 2012. Both of my parents had died in the previous year, so I no longer had to fear what they would do if they heard I was cross dressing or doing other feminine things. I guess their passing freed me to pursue feelings I had been experiencing but repressing for many years by then. I started underdressing, wearing panties under my male clothes. By the end of 2012, my wife knew, and begrudgingly accepted, that I wore panties under my clothes all the time.

Jan 2014, my wife passed away. I no longer had anyone to 'answer to' about my behavior.

March 2014, I came out to my daughter, who lived with me, and I seriously began to cross dress. Bought lots of clothes and makeup and learned to present well as a female.

July 2014 was the first time I went out of the house socially en-femme, and I loved it. No turning back after that!

[Brandie.n]

when puberty hit i started to wounder what it would feel like to be a girl i never acted on it.it was always in the back of my mind then when i was 15 i crossdressed as a witch for halloween heels,tights,elvira dress.been hooked ever sence

[crossdlalam]

well...........I remember.....8 yrs back
I was alone at home....I was not wearing anything....I watched myself in mirror...
I am slim and tall...........I thought of buying lingerie.......I was totally in different mood....it was A TOTALLY DIFFERENT PLEASURE....
I went to shop....but...I was hesitating to buy panties......but I saw....the displayed stuff....loll.........that made me to forget.....everything.....I brought it.....I wore it ...but I thought ....it wasnt ENOUGH......I need to get BRA......I went to shop ...but not sure abt......size....lol.....I told 32.....and yoooo. it was made for me
I took my photographs....posing myself....lol....for entire afternoon i kept on wearing ....lingerie
2 days back I broght some minies.....but I need to shave my legs...and pub hair