How did you start crossdressing and why?

[WillowWriter]

Well, I'll start, duh, hey.

When I was 10 years old a friend of mine, who was a girl, thought I'd look cute as a girl, so she dressed me up, and bam! I looked real for a 10 year old kid, I was a little guy then, and I had longer hair, so I got mistake by substitute teachers every so often. It was fun, and we did it a few more times as we got older. I think it was when I was 12 1/2 when we stopped, because she moved away. At that time it was so much fun, but I was at an alternative school at the time. I was having a lot of problems, being bipolar and all, so I couldn't say anything or I'd get bullied more, and probably get beaten up. So, I had to lay low. I crossdressed once in a while in my freshman and sophomore year of high school, but then, I met a friend who crossdressed during Junior year, and we had a little fun. After graduating from high school, my dressing needed to be fed because it was a good year since I last did it, so this winter I came out to my two closest friends. I was extremely surprised how well they took it. My friend Jo said she wanted to go shopping with me sooner or later, basically when I'm ready. So now I'm working on getting in better shape, my hair is already at a good medium length, so just need to grow it a few more months, and I'm working on getting clothes, so I'm doing a lot better than a week ago. :P My best friend still finds it kinda funny that I'm into crossdressing, but he has no problem with it, and Jo hasn't said much since, but she is really good to me. I love them both. ;) So...how did you start?

[AlannahNorth]

For me it was a long slow process. I was about 8 when I developed a real interest in feminine undies about the house, and things like earrings. I indulged occasionally as the years progressed, purged a couple of times, and only really got interested once my wife and I separated, years ago. It was an opportunity to try things in my own home without a chance of being surprised. Well, it led me to a new hobby! I've been laying low for about the past 5 years, but am now again enjoying things like skirts at home.

None of my friends know, it has to stay that way - a fact of reality for me here.

[WillowWriter]

Alannah, That's something. I'd be soooo much harder on me if I could tell at least my closest friends. You are strong, that's really good. You're lucking that you have free range with dressing, I'm not so lucky, only in the mornings for me. Mom and brothers go off to school and work, but I shouldn't complain.

[diannecourtney]

Oh, I got started much later in life, although there may have been hints as early as mid 30's when I found some spandex mens briefs. Wore em out and went to wife my girdles. Oh a time went by and the wife threw out her still lovely wedding truso - I travelled and they became wonderful nighties for a few months or so. At which time the Nehru look came in and the kid got 2inch heels. Well they died and eventually I saw a pair of ladies leg that I could die for and w/o knowing it I began to CD and find the forum and 3 yrs later the wife said she wasn't interested in a lesbian arrangement and cashed in the marriage. It has been fun ever since.

[Roberta Marie]

Willow,

First, to answer your question, the first that I can remember, I was somewhere between 6 & 9 years old and our family went to a cousin's wedding. Between the ceremony and the reception we walked to another cousin's house to change from our "church" clothes into some more comfortable (and durable) clothes. We were changing in my my older cousin Kathy's bedroom, and she left a pair of her pumps lying on the floor. For some reason I tried them on. They fit, both physically and mentally. Since then it's been a long (45+ years) road to self acceptance, but I'm finally starting to feel good about myself. I can't help but wonder how different things might have been if I could have had some help in figuring this out when I was your age. I think you are great for having the courage and insight to be who you are.

Second, I think it's great that you are finding some acceptance and understanding from good friends. Even more so, I think it's great that you were able to come out to them. You are awesome.

[WillowWriter]

Thanks Roberta, I'm glad you said that. You really made my day, thank you! I didn't have much of a childhood(Really rough life since I was 6 or so) I'm very big into knowledge so I looked stuff up everytime something felt weird or different about myself. Since I've been crossdressing a good while, I've managed to put a character into my book series(I'm a big time writer, plus I wanna get published one day) who is a crossdresser, and I like his character, very unique like myself, but I'm more like the main character, Kaz. Anyway... Thanks you for the compliment.

[AlannahNorth]

So, your situation has you exposed to some risk. Well, I can tell you one thing: the day you really let your guard down is when someone will walk in unexpectedly! I'm sure of this to the point that I would put money on it. That is something only you can decide for yourself, whether to be extremely careful and vigilant, or to be found out. What would happen if you were? If you search the posts here (they go back a long ways) you will find topics that may lead you to discover (carefully) how various family members would react.

I often read of CDrs who seem to want to be 'discovered' and pursue behavior that will eventually lead to this end. I don't, and so I only dress when the situation is suitable (read SAFE). Once again, not my preference, but a necessity.

Being strong is often not a matter of choice. If I could go back in time with what I know now, my life would be very different. I would not likely be as strong, but my life would have been so much better. However, I do not have that choice, and I rarely ever sit there and wish it was all different - it would be a waste even more time.

So while I'm inside I indulge to some extent and enjoy the experience. Enjoy your mornings - and someday you will enjoy remembering them!

[AlannahNorth]

Willow,

By the way, you have something I've never yet experienced - you share this side of yourself with two (TWO - in bold) of your friends. That is FANTASTIC!

[WillowWriter]

I see what you're getting at. I understand what you mean. I shouldn't let my guard down lower than it is now, so I'll take what you said and keep it in my head. Thanks.

[WillowWriter]

Thanks Alannah, I try and be open with those two. I was really starting to kill me inside, always hiding stuff from them. :)

[Kim Welcher]

When I was 3 I had to wear some girl's underwear for some reason out of my control. Later on whenever I saw a show on television that featured a male wearing female clothes (like Bugs Bunny) I would catch myself asking "what would it be like to dress like a girl?" Some time when I was in seventh grade I waited till I was the only person in the house and tried on one of my mother's dresses. I've been dressing secretly ever since.

[WillowWriter]

That's cool Kim. Yeah, Bugs Bunny often crossdressed I noticed. It's great when you're all by yourself and have the freedom to dress up and have some fun. I stay upstairs, our main floor has too many windows. :P

[Roberta Marie]

If I could go back in time with what I know now, my life would be very different. I would not likely be as strong, but my life would have been so much better.

My life would definitely be different if I knew then (when I was Willow's age) what I know now, but I'm not convinced that it would be better. I have to wonder if I would even have met my fantastic wife or if we would have had our fantastic kids and grandkids. I've had a great career, and I'm currently in my second great career. Sure, it's taken me a long time to come to understand and accept who I am, and it's been, at times, a difficult journey. But it's been a journey that's had a lot of great times, too. And without both those difficult and those great times, I would not be the person that I am now, the person that it has taken me this long to accept.

To be honest, I don't know that I would change a thing in my life. I'm pretty happy with the way it's turning out.

A couple years ago I attended a Transgender Day of Rememberance. One of the speakers was a young transman who said something to the effect that when people ask him about being born in the wrong body, he replies that he was not born in the wrong body. Rather he was born in the body that God intended for him to be born with, so that he could make the journey that God intended him to take to become the man that God intended him to become. What he said gave me a whole new perpective from which to look at my life.

[joannemarie barker]

I was 10 or 11 when I saw my sisters one piece swimsuit hanging over the bath to dry.I tried it on and bang.I must've gone to the bathroom 15 times that day :) after that my sisters room was so much more than a bedroom :)

[zenfirefly]

Women's clothes are so much better than men's clothes. That's the bottom line. I started crossdressing when I was 16. It all started when I tried on some of my mother's old dance wear. Leotards, tights, stuff like that. I don't know what made me think to do this but I've been wearing women's clothes on and off ever since that day. Over the years, my desire to wear women's clothes has progressed. I've gone though many phases where I wanted to wear women's clothes, then I didn't, then I did again. In the end, the urge to wear women's clothes has won. As of January 1st 2011, I wear nothing but women's clothes. I do not own any men's clothes. It has been an interesting process. I have a lot of respect for everyone who shares their crossdressing experiences on this forum. It inspires me to continue to live my life the way I want to despite the expectations of what one should or should not wear.

[tinalynn]

I started way back in single digit age (4, 5?), when my older sisters dressed me up for fun. I remember trying on their clothes and my mom's clothes from age 10, or so. All I knew was that I loved wearing hose, heels, and dresses/skirts. I like the way they looked on me and how the felt/made me feel. I started going out when I was in the Navy, very careful not to be caught. (I would drive 100 miles just to get away from anyone that might see me.) On my own after the Navy, I dressed at home and went out as I pleased. It was great! But, looking back, I really wish I would have done more. I was very self-conscious about it when I should have explored it and learned so much more. The old adage 'if I knew then what I know now' sure does make sense! Now, being married with a son 2 months away, I can dress at home because the wife is okay with it. But when I travel for work, I get lost in the pink fog almost to the point that I can't wait to leave work! It is so much fun shopping, trying on cloths and shoes, and just plain walking among the living as a woman that I can't wait to go out of town! Odd, really, since I also love being at home with my wife...

So, Willow, take advantage of what you have with your friends now. Go shopping with Jo. Explore, learn, try new things... You may not always have the opportunity to do this, but you have it now. But please do be careful while you explore - understand that, in time, your friends may find it a bit too much. Work with them and they'll stay friends.

[Rachel Lea]

When I was 13 a friend of mine was dressed a a girl by his sister for halloween. I thought it was so cool, I was jelous, I wanted to dress that way. Then I found a pair of my mom's pantyhose in the basement tried them on and I was hooked, they felt great. After that I stayed home for family vacations and played with clothes all week. But at that age I did not stay in them long always thinking I would be caught. What I know now I wished I had been caught I then I could have come out.

[Foxy Lady]

I was 9 or10 and mom had a Playtex OBG laying out and for some reason I had to try it on. This went on for about amonth when she caught me. Instead of getting upset the next weekend from Friday afternoon to Monday morning I was dresses as a young lady. That was over 50 year ago and still hooked.

[Marge]

the first thing that got me started was moms one piece swimsuit i tried it on and felt so good couldnt believe how great if felt been crossdressing ever since.

[dana8656]

goes back to my early years, parents gave me a book "Everything you wanted to know about sex, but were afraid to ask" (my sex education), there was a section in the book about crossdressing, some boy put on his mothers angora sweater and how it felt, I just had to try it, and I liked it.

[KellyCD]

It's been over 20 years since I started so I'm trying to remember back that far....so if my memory serves me correctly...

I was 7 years old and my older sister who by the way looks like Rebecca Romijn's twin, was staying at our house and I remember seeing some of her clothes and was awestruck by them. I didn't wear underwear anyways (much fighting was done between my mother and I for that) but once I saw my first set of bra and panties for some reason I was compelled to put them on. So I snuck a bra and pair of panties into my room and tried them on and instantly felt comfortable. I looked in the mirror and thought I was "pretty". I had already knew at the time that "boys don't wear that" kind of stuff, and it was widely regarded as "gay" and "only fags do that" (I was born and raised in Kentucky).

[Veronica Lacey]

Hi WillowWriter...

As a young child my parents, brother and I lived in a rather small abode, a two bedroom 1,000 sq ft rancher. My brother and I shared a small room and each had a separate single bed; mine was pushed up against the closet. The closet my folks had was too small for all of their things so my mother hung her dresses and other items in the closet in our room.

Low and behold, over time I would find myself reaching into the closet to feel those soft, satiny dresses and just loved the feel. I would occasionally crawl up inside the hanging garments, enveloping myself in the satin or nylon and rayon. I felt very comfortable. I was about 7 when all that began.

When I was nine we moved into a larger house and I had my own room. I soon found some of my mother's old nylons and panties and, in my new-found privacy, I began the journey that has lead to where I am today.

Indeed, I occasionally ponder whether or not I would have engaged in dressing had my mother not had her clothes in our closet. There will never be an answer for that. Ah well. :)

Good for you for being yourself with some friends. I believe that life will not be so cruel to you as it has been for others who cannot find the means to come to terms with themselves and current family.

[Kate Simmons]

I started wearing my Mom's clothes. I began to have feelings that my generation inferred that only girls should have. I felt I had no other option but to look like a girl as much as possible to "legally" have those feelings. The rest, as they say, is history.:battingeyelashes::)

[susan2010]

The first time I remember I was 4 or 5. I snuck into my sister's room, took off all my clothes, and put on her white petticoat. Looking back on it I don't think that was the first time I did it. That was about 50 years ago.

[Lucy_Bella]

oh boy!!.. If the walls had eyes.. I would say my earlist memories of xdressing started around 3ish.. It was when my lil sister was over one years of age.. For punishment , my stepfather use to dress us up in her clothes and I mean even the panties at family events when we acted up.. I use to dress in them even after , suppose I didn't know any better but was caught doing it by my mother..

Every since then it has always been on my mind..

[suchacutie]

I was 55. My wife and I were going through her lingerie drawer. There were some things that did not fit her, but I had lost some weight so I quipped, "gee, they'd fit me, I think". That lead to, "now if I had stockings and heels I'd be all set". She said, "do it". That led to "needing" a dress. In heels and a dress it seemed that she needed a name, and within a couple of days the whole thing just snowballed and it became obvious that I had a feminine part of me that we wanted to learn about.

Tina was born and she is most assuredly alive and very well!

:)

tina

[Billie Jean]

:battingeyelashes:When I was around 4 or 5 my Mom used to let me and my sister wear her stockings with run before she threw them out. When I was around 13 I started wearing my sister's pantyhose and from there her clothes when she stayed with her friends. She had the same color hair as me nad had a shoulder length fall that with my bangs made me look a lot like her. I was slender and had the legs for it. My feet still are very feminine. When I wore her clothes I would have passed for a teenage girl. I experimented with her makeup and got good at putting on my face. Billie Jean

[sara1985]

I always for as long as I can remember called myself Sara. I tried to deny her for so long , but I can't keep her silent any longer.

[t-girlxsophie]

I was 10yo,and was a typical boy and had a good upbringing,so there wasnt any deep psychological reasons why I started,can just remember snooping around in my aunt's closet (I stayed there at w/ends) and I dont know what came over me but next thing i was wearing a bra,tights,my Aunts Maxi dress and pink Cardi,it became like a drug from then every spare moment,spent putting something pretty on ,here I am years later still at it:)

:hugs:Sophie

[Jolene]

I was 10 or 11 when I saw my sisters one piece swimsuit hanging over the bath to dry.I tried it on and bang.I must've gone to the bathroom 15 times that day :) after that my sisters room was so much more than a bedroom :)

Finding my sister's bra and pantyhose in her room and for some reason just having to put them on. These many years later I still remember how good and excited I felt. :)

[Kaz]

Early teens... I then spent 20 years thinking it was just fantasy stuff. Then a phase when I started to realise this was not going away.. then acceptance a few years ago.

[Dee Baker]

First i put my left foot in the pantyhose and pulled it up my leg, then my right foot.....

[Edyta_C]

Well my Mom wanted a girl. So for roughly 5 yrs, I was dressed as a girl and had long hair. My hair (I wish I still had it) was a honey blond and in long curls. Then My brother was born and he was handicapped. My Dad felt it was because he and Mom were going against God's will (what ever made them think that). So they started forcing me to be a boy. I was so mad for several weeks after my hair was cut. I always played with the girls in the neighborhood. I think that up til then, they thought I was a girl. I ran away with my next door neighbor girl Kathy, who dressed me as a girl. We escaped discovery for a while because they were looking for a boy and girl. Then I really was in trouble. I couldn't go to her house any more or play inside with any of the neighborhood girls.

Even since then I prayed to be a girl. I still feel that my Mom would have loved me more if only I was a girl. This feeling probably resulted from the attention that a new baby gets and the fact that my brother had been born blind. He got ALOT of attention. Sometimes, I felt ignored. So I always have tried to dress like a girl. I'm sixty now and realize partly why I have this desire. I lean toward transition but at my age and health, I can only try to spend enough time each week looking as pretty as I can. My dear wife tolerates this, so while we are together I will only be a part timer.

I still thank the girls on this forum for their understanding help and advice that have helped me keep me together mentally. So we'll be here for advice and what support we can offer to you Willow. I hope you have success in with your writing. It is a good way to keep your head together.

Hugs Edy

[Suzette Muguet de Mai]

I have no idea why, it just feels natural for me to crossdress. I was always watching female family members putting on make-up, I was fascinated with corsetts and step-ins. I tried them on when I was about 7 or 8 I think. Womens clothes and make-up have always been like a magnet to me so I figure go become some flux and be absorbed within the field.

[Marla]

When I fist put on my moms lipstick it got me sexually excited and that continued as my motivation for many years. But then it occurred to me that I really enjoy being female and now I couldnt live without all my femme things. Ive tried to stop at times but it just doesnt work! GOOD for me!

[Terry V]

We all seem to want to know ,why? I know when I first started I was full of guilt and could not accept that I was "normal" but even with that strong feeling I still could not stop dressing in the things that for me feel so good and so right for me. Today many years later I am at ease with myself and as a result when I dress I feel good about it and I guess that is the bottom line, feeling good about who and what you are. I would give a lot to have come to this conclusion much earlier than I did

[SusanQ]

I was 4 years old and my parents had an 8 year old foster child living with us to keep me company. At some point she dared me to put on her panties and petticoat. From that point on I kept looking for opportunities to wear female undies.

[missyvf]

For me it was my best friends mom that got me going into the cd'ing direction, not that she had any idea at the time. I was 12, going through puberty and had a crush on her. She was a part time hair stylist and would cut my hair in her basement. Often times she would just wear a nylon nightgown for comfort around the house. I would sit there while she was cutting and ogle the outline of her bra and panties through the clingy fabric. The stool that she would have me sit on was always placed right in front of the washer and dryer. On a lucky day there would be a neatly folded pile of panties on top of the dryer waiting to be put away. My thoughts would just run wild. So the first opportunity I had, which was feeding and letting their dog out while they were away, I immediately went to her bedroom and began my journey...starting with her panties.

[laurajade]

For me, I vaguely remember being in the hospital and seeing a nurse wearing something thin and white on her legs, namely her stockings. I kind of found myself fascinated with that, although I couldn't have been more than 5 at the time.

After that, I don't remember when or how, but I just started getting really interested in tights and pantyhose. Seeing girls at school wearing tights and being curious about it, sneaking pantyhose from my mom's room to try on (and they were WAY too big for me at the time), etc. After several years of that, I wondered how they would look and feel with some heels that my mom had. Then added the skirt, then wondered about makeup, and so on, and so on, and so on...

[Amanda22]

I was so young in fact that it is the most vivid of my earliest memories. I would lust after the clothing of my sisters and once in a great while hold them next to me or even try something on. Fast-forward several decades to last August when I came out of the closet to my wife of two years. Now, I dress about half the time, and we regularly go out together as "girlfriends." My wife is a dream come true in so many ways.

[LoriFlores]

I always have trouble remembering exactly when I started, I'm going to guess no later than age 8. I had always admired girls clothing and so wished to have been born a girl. I was always so jealous when the girls at school got to wear such pretty dresses and tights. My sister is a year younger so has always been fairly close in size. For a while I had been admiring her clothing as well, especially a pink tutu. One day when alone in the house I just had this idea came over me to try on some of my sister's cloths. I ran to her bedroom, found the tutu hanging in the closet, and with great joy slipped it on. As I'm sure we all remember this first experience dressed as a girl was such an awesome experience. From that day forward I would enjoy my sister's clothing whenever I had the chance. I don't know if my sister ever knew about my trying on her cloths. I was caught by my mom with some of my sister's clothing hidden in my room but she never said anything.

[loserjaxxy]

When I was little I would play hide and seek with my aunts. When it was my turn to hide I will go in
my grandma's closet and put on her clothes. Since then I would wear my families clothes until I
was able to buy my own.

[James Kaon]

OK here we go, I guess i joined this forum to see if I was just a fetishist or what. I hope this does not hijack what many of u have posted which comes across as very meaningful and with so much more intellectual integrity - not my intention - just saying why i do what i do... So ok I will try. I have a very vague memory of trying my mum's tights when i was a kid, but it WAS sexual. I emphasize because like i said in my intro post, I get the feeling that many people here are less disposed to it being a fantasy or sexual activity but instead a real sense of identity (please forgive if I am not right here). I do not feel this. i feel although very comfortable just wearing things during TV or film, it is basically an extension of a highly sexual nature. I liked to see myself in tights during pvt time (i guess i am trying to censor my words so i dont get kicked or attract unwanted spam?). But then 25 years later (had not thought about it since a 10 or 12 year old kid - i cant remember how old) with never even thinking about it, for some reason, I decided to try again just 3 months ago... I am 37 and maybe a little frustrated due to work, but wow, can that be enough to make me desire something as much? I guess I knew i would be turned on, but by how much I really didnt know. I have always loved girls in lingerie, so to try just seemed like a reasonable thing to do. I dont know... I am terrified of being found out, but not because i judge, but because I know I will be judged - apart from a few people I know who I am sure will be cool with (like one friend I told but she is a lil nuts in a wonderful way! although not at her own personal delight)

So now, after a few months of experiments, I found I love the bottom half, the panties, the tights or stockings. It is more of a kick I think for me, and I do not share the feelings of another female persona - I will again worry that I may offend, I really hope i dont - u may have noticed I am a lil paranoid :P Sorry if this is not the best place to speak what I have said...

J

[Vickie_CDTV]

James, no need to be apologetic. For many, it starts out as a fetish, and for some it is always partially or fully a fetish. Regardless of the makeup on this site, you are certainly not alone (statistically speaking, TV fetishism is far, far more common than TSism.)

[Stephanie47]

It's difficult to determine when cross-dressing actually started. It's a frame of mind. I remember putting on my mother's childhood jumper at my grandparents' home because I had no toys there. I wasn't permitted to go down to the basement at an early age due to grandpa's tools. If I had my toys or could watch inane cartoons, I probably would not have become a cross-dresser. I had no desire at that time to be a girl, be feminine or was encouraged. Later I got into trying on my mother's slips that she hung to dry in the bathroom. I enjoyed the feel of the material. Later I blossomed into try on her bras, panties, girdles, stockings, slips and dresses. I had a sexual motivation to dress then. So I had say, that's when I became a cross-dresser. Later when I had no opportunity to cross-dress, I had no urge or inclination to do so. It wasn't until after I was married for awhile that the 'urge' returned. With maturity cross-dressing lost the sexual component. Right now I'd say cross-dressing allows me to shed my maleness when necessary to help cope with the horrors I experienced in war. If there was ever some therapeutic value to cross-dressing, that's it! That's probably the reason I will never stop cross-dressing.

[BillieJoEllen]

As far back as I can remember I thought of myself as a girl. I think a few people had insight into my way of thinking. I had on numerous ocassions been underdressed and fully dressed up until I was in the fourth grade. When I was in the fifth grade I went to our school's Halloween party dressed as a colonial girl. My sister wore that dress about three our four years prior to that. My mother wanted to get a little more use out of it. I don't think I resisted. After Halloween a girl told me that I still didn't know what it felt like to wear a dress because I had pants on underneath. What????
Being home alone one evening and being bored I thought about what she said and decided to see for myself. So I tried the dress on again this time without my pants. Oh...OK, big deal. Didn't think anything more about it until I overheard my sister talking to my mother about her new corset that she was going to wear under her prom dress. Once again curiosity got the best of me and when I was alone again I tried the corset and dress. Not having a lot of time I decided that I would try it again at a future date. I somehow got it into my thought process that I would try on a pair of my sister's panties also. Once again....oh, ok.
Overhearing some girls talking at school one day one of the girls told another girl how special she was feeling in the clothes she was wearing. Hmmmmm....
The clothes she was wearing were all the usual undies for that time period. a sweater and a tight skirt. I thought that if I ever had the chance again I would try dressing that way. (I could've given up any thoughts of ever CDing again at that point).
One night my sister and parents were out. I went to sis's room. Got the needed clothes. Tried them on. OMG!!!! From that point on I was hooked! It was the tight skirt that did it for me. Looked forward to everyone being out of the house from that point on. Managed to keep everything a secret for about three years until I got caught. Found out everyone suspected what I was doing all along.

[Angelofsomekind]

I was about 10 or 11, at a friends house, his mom left a bra in the bathroom, I have no idea why, I just had to try it on. Then I had to get panties, once those were on, that was it, I was hooked! From there I'd get what I could from various places, but being older and close to my size she always had the best stuff!

[Melinda Lou]

When I was 3 I had to wear some girl's underwear for some reason out of my control. Later on whenever I saw a show on television that featured a male wearing female clothes (like Bugs Bunny) I would catch myself asking "what would it be like to dress like a girl?" Some time when I was in seventh grade I waited till I was the only person in the house and tried on one of my mother's dresses. I've been dressing secretly ever since.

I've posted about this before (this thread seems to get resurrected every few weeks), but my experience was similar--when I was a little boy, I had to wear my cousin's panties once (just once!) for reasons beyond my control (needing clean underwear and not having any away from home, basically). This turned out to be a formative experience--once puberty started to hit, so did a need to crossdress, mainly underdress, and "girl clothes", especially panties, have been a presence in my life ever since (for...about 38 years now?).

[MWCMDarlene]

For me, I was 12 years old. My parents were seperating at the time, so me, my sister, and my mom were living during the summer with grandparents until parents could decide what they were going to do. I was going through early stages of puberty, as I recall. One day, I read "Dear Abby" in the newspaper and she was responding to a letter about some man wearing women's clothes. I was intrigued, for I had a friend when we were 5 or 6 who used to play "dress-up" in his grandmother's box of old clothes. One day, I was mowing an uncle and aunt's yard and had a key to the house so I could get a drink of water. While getting a drink, I noticed the laundry, just washed, sitting on the couch to be folded. On top was a bra belonging to my aunt. I put it on over my shirt to see what it looked like. Each time I mowed their grass, i went in, found a bra, and would put it on, but each time under my shirt and then would begin stuffing with washcloths.

That fall, while sister would be at friends house and mom at work (we had moved out of grandparent's house into our own) I would put on mom's bra and pull-over white shirt that had snaps at the crotch. Oh how I loved that shirt. One evening, sister came home while I was wearing bra and that shirt, but I was able to conceal my "boobs" in a way that I don't think she knew except the look of panic on my face and sweat breaking out on my forehead. Since then, the most important garment of my crossdressing is a bra and on occassion, I will underdress with panty's.

[tommi]

My mothers nylons and Leggs pantyhose the egg would make for a great set of falsies at age 5

[Lorna]

I am envious of those who had sisters around them when they were growing up. I didn't and so my childish natural curiosity about the opposite sex did not really get going until my early teens when girls changed from being simply other children in different clothes to fascinating and attractive young people wearing very interesting clothes. The very clear demarcation between child and teenager which most girls (in the UK) displayed by starting to wear nylon stockings, the boldest of them even to school, really sparked off my interest. I was about 13 and my grandmother, who had lived with us, died, leaving me the freedom of a house with no adults at home in the daytime. I really wanted to know what it was like to wear what girls my age were wearing but I had no access to such clothing (no sisters) and so I tried a skirt of my mother's and put on some of her old nylons. It was a very enjoyable experience and I repeated it on several days when I got home from school. Of course, I knew that girls held up their stockings with suspenders but was not at all sure whether they wore belts or girdles. I could judge only by what was on view on washing lines where girls lived and by what I saw in advertisements and in shop windows. Wearing the nylons was good but with nothing to hold them up it was not ideal.

Watching some girls walking to school (we had only single-sex schools where I lived - so no sisters and no girls around me at school either!) I wondered what it must be like to have nylon stockings stretched tightly over your legs. Naively, I had no idea whether they made it more difficult to bend your knees - but I wanted to find out. In the bottom of my mother's drawer was an old and obviously no longer used Gossard girdle. It was pink, had quite a high waist fastened with hooks and eyes, made of coarse elastic net with some kind of stiff cotton material for the front panel. There were a few bones around the top. It didn't fit me - a bit too big - but I could fasten a trouser belt tightly round the girdle waist and that was good enough to allow the stockings to be attached to the suspenders. These were non-stretch stockings which came barely to the middle of my thighs. I knew then (or thought I did) how those girls actually felt. It was a bit harder to bend my knees and when I sat down I could feel the girdle stretching (even though it wasn't at all tight) and I noticed how taut the back suspenders were.

Next day, as some school girls sat down near me on the train, I watched them with new interest knowing what it felt like to do that wearing those clothes. Of course, over the next few years, as I got to know quite a few girls rather well, I learned that their stockings and apparatus for holding them up came in many varieties and I developed even greater fascination for all aspects of women's dress. It would be many years before I was able to try wearing a wide variety of underwear and other clothes but that's where it started and it's still with me.

[NicoleScott]

James, I agree with Vickie's response to your post (#43 & #44). We crossdress for different reasons, and dressing because it's sexually exciting is nothing to apologize for.
At around age 5 I loved to look at magazines and catalogs and see the pretty women wearing pretty things. At around age 8 I started putting on lipstick behind a locked bathroom door, and around age 10 began wearing my mom's & sister's high heels in private. I began to dress fully in my twenties. It started out and remains exciting. I never wanted to be or thought of myself as female. Just a part-time dresser, for excitement.

[Andria]

When I was around 8 or so, I remember going to the grocery store with my mom, and a few occasions hearing women tell my mom, "You have a cute little girl." Or something similar. I can see how they mistook me for a girl. My hair was to my shoulders, and my face looked a bit girlie. I didn't think much of that back then.

I didn't dress until the age of maybe 11 or 12. I was home alone during summer school, got bored, and tried on a red one piece bathing suit (don't remember if it belonged to my mom or one of my sisters). I looked in the mirror and was amazed. lol Even though I was a young boy, I had some booty back there. lol Plus, my hair had grown longer, and I loved what I saw. I remember going in our backyard just to walk around dressed like that and looking at my reflection in the dining room windows.

My love affair with my new found female self escalated rather quick from there. I wasn't always smart about it as I was still young, and I'm lucky no one ever hurt me. But that's another story. ;)

So that's how it started for me. ;)

[Jessica86]

I was about five. Older sister always wanted a younger sister. So, she dressed me and treated me like her younger sister. This went on for years and years. Then, when I was twelve, she moved out, and I kept some of her things. Just never left me. It would go away for a few years, then one day I would think "Hey, I still got that stuff in a box in the closet....hmmm.."

[sissystephanie]

I was somewhere between 6 and 7 when I put on a pair of my older sisters panties to see what they felt like. I was "hooked!" That was some 70 years ago, and except for 2 periods when I stopped completely, I have been dressing ever since. Included in that time period was almost 50 years of marriage to my dear late wife who knew I was a CD, and totally accepted and supported me as such!! Life is grand, could only be better if I still had her!!

[sara1985]

My experience was different. I had never dressed until I was in my 20's. I was in the military and shopping at the PX, I was walking through the womens department, to get to the electronics department, when I saw that dress and I had to stop and look at it. I just had to buy it. I can't explain it but that was the first time Sara let me know she was there. I tried for years since to deny that she was there, I can't tell you how many times I have purged and threw every piece of her clothes I threw away. I recently came to the realization that she is part of me and I can't deny her any longer. I'm still figuring it out but I'm happier than I have been since I can remember.

[Vicky Peters]

I was staying at my aunt's house for the weekend and she asked my to zip up her dress. I did, but wondered how she got dressed (hooks in back and zippers on the side). Next weekend I discovered that she was wearing a long line bra and side zipped girdle. Got caught just once and it was our little secret.

[NicoleScott]

Sara, what an interesting story (post #56). I like to read how others got started. Many stories are similar, mostly (but certainly not all) going back to childhood experiences and desires. But I've never heard of such a sudden onset of crossdressing. Sara just jumped out of you. Wow. I guess it just proves that while we may have some similarities, we are all unique.
So much for "how". As to "why": if anyone figures it out, please let the rest of know.

[Maria 60]

I think it was about 7 or 8 years old, we had our grandparents living with us, so me and my sister would have to share a room. She would always leave things laying around. I only remember laying in bed and seen a pair of pantyhose on the floor, so i covered myself under the sheets and put them on. WOW! what a feeling, since that day i always have a pair of pantyhose in my possession.

[Billie1]

This has been a very interesting thread to follow. While I believe that we are all unique and wonderful individuals, the similaraties of our early experiences reinforce the feelings of sisterhood and community that we share. Long live the sisterhood!

For the "when" part of the question, that's easy. I was in sixth or seventh grade, and was having a week-end sleepover at a friend's house while my parents were away. He was part of a large family (9 kids) and I did not have a sister. We were getting ready to turn in, and I noticed a ballet-type leotard with a tutu in the laundry. It was a strechy-type material, and the stiff tutu stood straight out. I had never seen anything like that before.

That's the "when" part. As I said, that was easy.

To continue, the next thing I knew, I was sliding my legs through the openings, and pulling the straps over my shoulders. Why, I had no clue. All I can remember is, I stood there several minutes, staring at myself in the mirror. I don't know why, but I was riveted to the image of my shape, now highlighted by this clingy, strappy garment I was wearing. With no understanding of the new sensations now coming over me, I stood there for what seemed like an eternity, smoothing the material over me. In my new-found excitement and enthuisasm, I then went back to the 'boys room' to share my fun with my friends. Don't know why I did that, either. That's when I found out about the importance of being discreet, too.

[JamieTG]

I was about 5 years old and saw a pair of my sisters panties laying around. They were a pretty blue nylon with white lace around the leg openings. With no real thought or reasoning ability at that age I had an immediate strong urge to try them on. They felt wonderful and I was hooked from the first time. It wasn't long before I was sneaking into her room and trying on other things. The main reason I was doing this was that I loved the way the clothes felt against my skin. I wasn't trying to look like a girl. I just loved the soft, silky feeling of the clothes. I also felt a strange excitement from the "taboo" factor. It was exciting to be doing something society didn't approve of if that makes any sense.