How Did You Get Started

[Cristy2]

I'm sure there has to be a thread on this already, but how did you get started crossdressing? Myself, I've been crossing for as long as I can remember and I honestly don't remember how or when I got started.

[Sabrina133]

Middle school. First tried on my sisters skirt and matching top --- just couldn't stay away.

[kimdl93]

There was literally one posted by the identical title just a few days ago. Search for it.

[xd-tigger]

It started when I was four years old. Saw my sisters skirt on the bedroom floor and tried it on. Got caught too.

[heatherdress]

My wife insisted that I buy a pair of high heels.

She knew I liked when she wore her heels and wanted to know if I would enjoy owning and wearing a pair of my own. I purchased a pair of black stilettos, tried them on in front of her. It was great - exciting, different, sexy, fun. She then gave me some nylons and underwear. Each step was better and more exciting. She then used makeup and spiked my hair with gel. I was shocked and loved it.

We talked a lot. Assurances, discovery, intimacy, pleasure, fun. She is very happy she initiated and supported and enjoyed my crossdressing.

[Stephanie47]

I can't exactly remember my age, but, it was as a single digit kid. My mother always hung her nylon slips to dry in the sole bathroom of the apartment. I loved the feel of the nylon. I use to take them off the clothes rack and try them on, dry or wet. It didn't matter. Later, as I became more adventurous I added her bras, ugly panties, girdles and stockings.

[Cheryl Ann Owens]

I was maybe 4 years old and slipped on my grandmother's dress. It's all a blur but the next couple years I was fascinated by my sister's clothes and they even did my nails with polish and it was suddenly supressed. When I was 12 something "clicked" in my head and I had a sudden desire that felt perfect and right. Having a couple hours to myself after school I would try my sister's clothes and that, as Paul Harvey used to say, is the rest of the story until I leave this planet.

Cheryl

[Beverley Sims]

I had three girlfriends encourage me.
We all then shared a house and they would dress me up to make a foursome.

[irene9999]

I started in high school trying on my mom's/sisters clothes. I was really really skinny as a teen so her clothes fit me perfectly, I liked watching my legs in the mirror and thought they looked as good as other girls

[JamieOH]

I can remember having the urge to wear dresses and pretty girl things from about 4. When I was about 8 or 9 I took some of my sisters clothes and would wear them late at night while everone was asleep which I did as often as possible for many years. . I especially loved this one pink chiffon nightgown. I would wear it and watch Soap which was always on very late because of its controversial content. I loved that they had a CD on that show. Helped me to not feel so alone and abnormal.

[Beth Wilde]

A friend at school encouraged me to try on his sisters tights...... Never looked back!

[Seana Summer]

I started by trying on my sisters pantyhose. I was maybe 3 or 4, not yet old enough to go to school. I have no idea why I did, but I liked the feeling of nylons ever since.

[AmandaM]

I was about 4 years old. Wore my sister's clothes.

[anneob2002]

Slips when I was 4 or 5. Oh what a feeling!

[Krista1985]

First time in my mid teens was a one-off,

Found my girl cousins bra hanging from a towel rack in my bathroom and had to put it on for some reason. I really enjoyed the experience as I had developed small moobs that made the tiny bra fit snugly. "It" didn't happen again until grad school. Now dressing is a regular occurrence.

[Sister Rachel]

Granny's knickers aged 3 or 4. Making pyjama jacket into a skirt aged 7 or 8. Trying on stepmother's bra, panties and tights at 12/13, sneaking home to fully dress in her clothes at 16/17, occasional and often ill-fitting purchases from catalogue during my 20s ...

[Jilmac]

I've said this in several threads before but it's worth another say. At around age 7, an older cousin dared me to wear panties and a dress. I took the dare but was scared of being made fun of, which my cousin did when he saw me. Even though I was frightened by his teasing, I loved the feel of the panties and look of the dress, and I was hooked. I also had three older sisters and plenty of clothes to experiment with, and that gave me even more reason to love dressing.

[Robin777]

I started dressing when I was 12 or 13. I got attracted to my mothers underwear. then I started wearing her bras and slips and other things, pantyhose,garter girdle and stockings. Then I started putting on her dresses. It just felt like the natural thing to do. I remember I was attracted to women's clothes at an early age. Looking at them in the Sears and Penny's catalogs. I remember I always had a fascination with them.

[Cristy2]

I used to dream of being a fashion designer, but I can't sew worth a crap.

[franlee]

I was 16 and dared my girlfriend to exchange clothes to get her out of hers for "fun," well it worked and started a long chain of events for the last 43 years or so!

[Kate Simmons]

My Mom's panties when I was 5 and it escalated from there.:battingeyelashes::)

[Requal Jo]

My sisters dressed me as a girl from age 3 to 6 years and took me out with to play with them. Had a break for a few years and got the feeling again for a couple of years, then stopped for while to have a family. Kids grown up and left home so got the feeling again. Requal.

[aitun]

I started in high school trying on my sisters clothes. I was really really skinny as a teen so her clothes fit me perfectly, I liked watching my legs in the mirror and thought they looked as good as other girls

[Tina B.]

Age 6, sisters white nylon slip with lace around the bust, and white nylon panties. Wasn't my fault, she left them in the bathroom, I just happened to find them.

[edith]

My mom's underwear and makeup at around 6.

[Frédérique]

I'm sure there has to be a thread on this already, but how did you get started crossdressing?

I put on the thing that I had always wanted to put on, when (at last) I had the opportunity to do so. In many ways I had already cross-ed the threshold long before I ever slipped on the skirt, but the latter was the start of my crossdressing...
:battingeyelashes:

[wilt575]

My sister who is ten years older than and her girl friends me started dressing me when I was about six. My parents traveled a lot on business etc. and left her to incharge. They had sleep overs and parties (grandma lived next door but pretty much let us be, but was there just in case) and I was always one of the girls. She bought me some clothes and her friends gave her there younger sisters old clothes. As I got older I liked the girl in me, dressed when ever I got the chance. In all the years I've never looked back and felt it was wrong!

[Milli Montanari]

I started with my mother's lipstick when I was about 7. I then began accumulating her discarded makeup which I kept in a cardboard box along with a Max Factor how-to booklet called "The New Art of Make-up". Also made myself a "dress" out of an old flour bag with cutouts for arms and head.

[stephNE]

Starting at about age 5, I remember putting on my mothers bras and panties. Of course they were huge on me, I wore them right overtop of my boy cloths and would go off to my room and play.

[BLUE ORCHID]

Hi Cristy, I guess that it all started when I was three days old and my mom dressed
me in that little white receiving dress when they brought me home from the hospital.
I have been dressing for at least 66yrs.

[Cristy2]

LOL! Maybe that is where I got started. Thank you to all of you for your in puts.

[DebbieL]

One of my earliest clear memories was a time when I made a "dress" out of a dry cleaner bag. I was about 2 years old. My mom even made a little belt for it, and I wore it until my dad came home. He wasn't freaked that I was wearing a dress, he was freaked because he was afraid I might have suffocated in the plastic bag. Even before that I would make skirts out of towels, and one time I even made a dress out of a pillow case (mom wasn't happy about that).

Transsexuals often start much younger and don't become AWARE of themselves as cross-dressers until someone tells them that they have to STOP cross-dressing.

I remember going home after school in 1st grade, and we'd swap clothes. One of the girls was as curious about my stove-pipe blue jeans and flannel shirts as I was about her dresses and tights. We did this for several days, trading clothes with each other, until the mother came home from work one night and saw me in her daughter's pretty dress, including panties, tights, mary-jane shoes, and looking like a happy little girl - with a buzz cut.

I didn't understand the difference between boys and girls and just wished my parents would let me grow out my hair so I could wear a dress and be like the "OTHER GIRLS".

When I was caught, the mother called the PTA, teacher, and principal, and told them to make sure I didn't play with girls anymore. I tried to play with the boys, but by the second day they were throwing rocks at me and hitting me with sticks when we got off the bus. I withdrew, stopped participating in class entirely, and refused to read out loud. I got moved to the "dumb side" of the room, and the "smart side" started reading the book I had been reading when I had left my old school. At that point I realized I didn't belong in that SCHOOL, let alone in my BODY, or even in my LIFE.

To cope with the loneliness, I started reading. Books about girls made me sad because I wanted to be one and couldn't. Books about boys made be sad because I didn't like being a boy. So I read lots of non-fiction.

I missed being pretty with the other girls, so I would fish mom's church clothes out of the dirty clothes hamper and lock myself in the bathroom, sometimes for an hour or more, dressing up pretty. Eventually, mom caught me (she couldn't wait any longer so she unlocked the door with a coat hanger and saw me in her clothes). I broke down crying, telling her how much I wanted to be a girl, and how much I hated being a boy. She tried to comfort me and even offered to buy me a pair of tights the next time we went shopping.

When she told her therapist about me, she was shocked to find out that the "cure" for this was electro-shock and if that didn't work, a lobotomy. There were a few times later on when she caught me in her clothes and screamed "Do you want to end up a vegetable?". I had no idea what she was talking about. I never did stop dressing, and eventually was correctly diagnosed by a qualified therapist as transsexual. I knew I was transsexual from the time I was 5, but I didn't know what that was.

[FrillyShelly]

I actually got started from an episode in Scouts.... I think I was about 10 where I played the part of a girl for the annual Christmas play. My Mum helped with & borrowed all my sisters stuff, pink polkadot dress, strappy court shoes, makeup, ribbons in my hair the whole 9 yards. I was soooo sooooo nervous because it was in front of EVERYBODY !!!! but I LOVED it and got hooked.

[Meg East]

I started when I was seven or eight with my mother's used dresses, bras and panties. I found I liked it. Having the entire basement to myself gave me the time and privacy to experiment. That in a nutshell is how I became the man I am today.

[Julie Denier]

I started clomping around in my mom's shoes as a young boy, then started experimenting with other clothes throughout my teens. Little if any dressing from there into adulthood, though always remained curious. Dressed fully for the first time (wig, makeup, lingerie, dress & heels) when I was 38 (pushing 41 now) ;)

[NV Susan]

Started when I was 7 or 8.:eek:...wearing my sisters cloths. Why, all mine were in the laundry......:heehee:

[Debutante]

I was eleven years old and home alone.
I was mysteriously attracted to my mother's closet, and her dresses lloed wonderful.
I tried them on........ and have never been the same since!

[ellieg]

I started wearing my mother's underwear when I was a teenager, but not too often so as not to be caught. My dressing re-awakened when I met my now-wife and had access to her closet.

[Joy3]

A neighbor girl [Cathy} liked to dress me as her girlfriend when 5 or 6. We would do it at her aunts house, I loved it!

[Diedre]

My mother use to have me wear her wig to style and comb out. And when I was 12/13 she used me as a dress model for alterations and sewing that she took in for added income.

On more than one ocassion she would think nothing of having me wear a stuffed bra or a girdle with nylons so I could wear heels while she did the hemming.

Unfortunately I started showing a little too much interest in the role and would stay dressed in the lingerie a little longer than I should have after the fitting. And I was soon replaced with a dress form she got from a second hand store.

Evidently at some point my mom voiced her concerns about me to her sister and my older girl cousin must have over heard the conversation as she asked me about being the dress model and if I would like to dress as a girl with her sometime. She kept it our secret and I had many fun sessions dressing up in mid late 1960's styles of a girl my age. Thanks cousin

[texasm31]

I started clomping around in my mom's shoes as a young boy, ;)

I totally forgot about those days. I always think of clothing, but it did probably all start with shoes.

[anneob2002]

Wow.

You know, when I was a kid, I probably would have called you names and not played with you.

There are so many ways to be born into this life and being transexual is one of the more misunderstood and I think harder things to deal with.

[Sarah Beth]

I was 13 and had a huge crush on this woman in her early 20s who live a couple of blocks from us. Almost every day I was over at her house doing lilttle odd jobs around for her. One of things I would do was help her hang her clothes on the line. She always looked so amazing to me and I loved how she dressed.

We were taking down the clothes one day and she said to me it looked like I really enjoyed touching her things. I didn't know what to say back to her so I just stammered out something about how pretty she looked in them.

A week later she was in the house and I was taking down some things she had hung out earlier. I was very conscious of what she had said the week before. I noticed she was watching me from the window so I hurried up and took the clothes on down and took them in.

I was really embarassed to think she had "caught" me fondling her things. I started to leave but she asked me to sit down at the kitchen table. She asked me if I just wanted to see her in those things or if maybe I wanted to be in them myself. Then she told me her brother dressed in women's clothes and she thought he looked really good sometimes doing that. I didn't know what to say because I really wasn't sure what I wanted.

A week later I was dressed in one of her outfits. It felt so natural to me. After that about once a week I would go over to her house and she would dress me up. She never did makeup on me or anything.

A little over a year later she left town but she left me a few things. These I purged not long after.

[AltairaMorbius]

When younger I remember my Mother used to run around the house in the morning in just bra and pantys, it was the 60's so lots of Vanity Fair pastel briefs and heavy duty white 4 hook bras, every Saturday like clockwork she also used to wash and hange her bras and panties to dry in the bathroom. Did I want to make love to her, no, I wanted to be just like her. One Friday night, my heart pounding, I slipped into some things from the hamper, they just hung on me but were so soft and pretty. As timed passed I started to take my time and try on several things, enjoying the matching sets most. The damp gussets touching me were magical!

[DonnaA]

The desire to crossdress must be genetic. I am absolutely convinced of that. Some of my earliest memories (3-5 years old or so) are of my desire to crossdress.

I went all through catholic school (K-12). Of course, the girls wore uniforms, including nylon knee-high stockings, tights, and (later on) pantyhose. I remember being in school and looking at the girls wearing these "great things". I remember being "aroused", but I didn't really know why. I was just a kid. And I remember having a tremendous, burning desire to wear those things. I didn't really fully understand it.

I remember being in the first grade, when I was 6 years old. I asked my mother if I could wear nylon stockings/pantyhose and panties to school. She replied that only girls wore those things. I kept asking her, several times. She was getting more and more annoyed. I finally stopped asking. I was only 6 years old, but I remember being so upset that I couldn't wear pantyhose and panties to school.

I started wearing my mother's nylon stockings at a very young age, maybe 5-8 years old or so.

I eventually "graduated" to wearing my sister's panties, nylon stockings, and tights. My sister went to catholic high school, and she wore pantyhose to school every day. During that period of my life, I would put on her pantyhose every day - when no one was looking, of course. It felt so good.

I finally started buying my own "things" when I was in college.

[Dani0948]

When i was about 9, i frequently played dolls and dressup with my 2 younger sisters. What i remember most vividly was trying on a pair of high heeled pumps given to us by our next door neighbor. I was really sad when i outgrew them.

[Joy3]

When I was about 5 or 6 a neighbor girl [Cathy] said she wanted me to be her girlfriend. She dressed me in her clothes and we would play girl games. I really enjoyed our play together. As I got older I began to wear my mothers things. Remember stuffing a bra, putting on some lipstick and a kerchief[scarf] over my head and going for walks in our neighborhood. Loved it when guys would whistle at me. Have been hooked to this day!

[Laura912]

One stocking, those old ones with seams, at a time. Still can put on a pair and have the seams straight.

[mandimoore]

I was about 8 years old when I found my mom's lingerie drawer. I was so amazed how soft it felt to have that silk slip on my boyish body. I then graduated to my younger sisters bra and panties. I also stole satin bra and panties from my beautiful step cousin who was still in highschool.

[Jaymees22]

The first time was for a second grade play "Cinderella", My friend and I played the ugly sisters, obvious type casting. I dressed again when I was 17 using my mothers clothes and wig. Then I took a fifty year break and started again a little over a year ago. I finally found myself and I'm loving it. Jaymee

[Joanie_Shakti]

I'm sure there has to be a thread on this already, but how did you get started crossdressing? Myself, I've been crossing for as long as I can remember and I honestly don't remember how or when I got started.

I've been thinking a lot about this lately and I've come to the conclusion that it started with the satin edging on my security blanket when I was a young child. I've had a thing for satin since I can remember and I think it started with my blanket. Since I would suck my thumb while smelling the edging, I wonder if that had to do with being breast fed and my face up against satin slips and nightgowns as an infant.

Around 5 years old, I can remember being fascinated with the silkiness of my grandmother's nylon covered legs. This was in t he early 1960s, where most women wore nylons and heeled pumps.

Later, I remember my mom letting try on her wigs on a couple of occasions for a few minutes. I still have a picture from one time. I also tried her lipstick a couple of times.

But when I was about 13 years old, I caught my brother trying on our mom's pantyhose. I had never thought of that before and joined in, trying on her nylon panties too.

I was hooked. Started sneaking her panties and even wore them to school on occasion. Got talked to by my dad a couple of times for taking them. He had also found some I had ordered from Penney's through the mail.

After I started working, I bought my first bras, dresses, skirts, and shoes, both by mail and in stores in other towns. But I wasn't very good with size or style. I would also often buy pantyhose from Circle Ks in town but in other neighborhoods.

Then about five years ago, my dressing started picking up. I wear makeup and wigs more often and have way too many shoes, most of which are pumps. A few years ago, I even outed myself to one GG friend whom I sometimes video chat with.

[Amanda63]

This is a great question....
My earliest memories of being interested in female clothes are about 10, one day I found myself very intrigued with my moms under garments, looking back I have no idea for this. Even at this early age I found myself trying on the bra's and pantys which both felt natural and made me feel good. Looking back I still find this very interesting and really have no explaination for wanting to do this.

[Joanne108]

Well I talked about this before, so Ill talk about my first total dressing. One Halloween I stayed home and handed out candy because I was too cool. One of my friends came to the door dressed as a girl. It must have been a common idea that year there were several guys that were dressed as girls or women. That awoke my earlier memories of wearing a bra as a 5 year old. The next day was a Saturday and I could not get the idea of dressing as a woman out of my head. Everyone was out for the day but me, I found myself in my mothers room. I dressed completely as a woman. I put on a bra stuffed it put on her corset and stockings then her black dress and hi heels. I put on my mother's blond wig and make up. I looked at my handiwork in the mirror and was hooked. I thought I looked good. I stayed dressed for an hour or so but it felt great.

[katie1000_uk]

I was about 7 I think and tried my sisters clothes on...loved it and it has just evolved from there! I guess life would be simpler and less expensive if I wasn't a CD, but not as fun!!

[Candice Mae]

Due to a hormone imbalance during puberty, I got gynecomastia and a feminine figure. After a a few months I needed a bra, and stole one from my sister. Then my sister persuaded me to try on one of her dresses, I was amazed with how I looked. After that I started dressing on my own, learning how to perfect feminine image. A couple years later nature and testosterone took its course and masculinized by body, but lucky I still have some of my curves.

[Megan b]

It started with a pair of pantyhose when I was about 12/13 years old and just progressed over the years to complete transformation when ever I feel the need or just want to feel fem. Now in my mid 40's I've excepted and like this side of myself.

[immike]

I was about 4 years old. Wore my sister's clothes. I have been wearing Mothers clothes
for years,I'd wait for her to leave in the morning for work&try on all her dresses,slacks,skirts,blouses&I ordered pantyhose online
and had it deliverd to me,so I could slip into a pair in the morning&just wear all of Mom's outfits&her heels

[Christina89]

my moms old bikini

[Lori B]

I discovered my Sister's closet:)..........50 some odd years ago:doh:

[jodie k]

guess i was fully dressed with lipstick when i heard the key in the door. I scooted under the bed fast, but my sister found me there.

But i was doing semi-things as long as i can remember....:brolleyes::brolleyes:

I started with skirts fulltime at home after seeimg a newspaper photo of men in skirts marching up to the Metropolitan Museum of Art to support or just inspired by a Braveheart costume exhibit. Guess that was 1996. I had just separated from my wife, who now gets skirts for me.


and gee i just found the icons on the side of th:devil:is message.

[Lorileah]

similar thread already ongoing @ http://www.crossdressers.com/forums/showthread.php?187692-When-did-you-first-crossdress.