at what age did you first crossdress?

My earliest memory of dressing was around 11 or 12 I think. I can remember trying on a pair of my mums knickers and an old pair of tights. The first things I bought for myself was a pair of stockings and a suspender belt when I was 18...wasn't I brave?!! After that I started, and somehow managed to keep secret) a small collection of knickers and bras, and even a skirt.

After I married I managed to suppress it for a few years although the need (urge??) never really left of course and I soon started to "sneak" wear whenever I could. Eventually it came out and my then wife was actually quite relaxed about, to the point where she would shop with me for undies.

Subsequently we separated and my first g/f afterwards was also ok with my wearing and actually used to raid my knicker drawer...although I have to say I used to raid hers too!

Now I live alone and I've got loads of bits and pieces now. I've got some very nice girly nightwear which I always wear, I've started wearing strappy vest tops under my everyday clothes and I've revamped my undie collection.

My latest development is to start painting my toe nails (either clear or pale pink...I'm not that brave yet!) and I'm really thinking its time I bought some sexy heels...:battingeyelashes:

The first time I wore girls clothes was when mom dressed me in my sisters clothes, I guess I was about two. The first time I did it to myself was I think three or four, when I wanted to be a 'big' girl like my sister so I could go to school too, but I didn't connect it to any sexual role difference. The first time I connected it to being gender and role different was when I was dressed up by my abuser, as he was teaching me how to be his girlfriend. About a year after that when I was 8 I started playing with my sisters old clothes on my own when no one knew, wondering if I was really supposed to be a girl. When I was dressed as a girl, looked in the mirror and saw a little girl looking back at me, I was shocked, and the confusion as to what I was remained for many years.

I was about 8 or so i wore my cousins clothes dresses and white cotton knickers well it was the 80s

I love this question now although it used to intimidate me.

I started at the tender young age of 50!

Right time, right place in life...


viva the late bloomers!

Cassie

I was about 5. I remember mum put a extra wardrobe in my bedroom full of her clothes, cause she had no room in her bedroom, and I used to like brushing myself against the fabrics. As I grew year by year I'd try them on after dark. I used to love mums nightgowns....they were so femme, flowing and had an old victorian feel to them. When I used to come home from school aged about 12. It gave me half hour time by myself, before mum came home so I used to put her nightgowns on. Great memorys.

i was about 10 years old when i started to wonder what it felt like to wear a dress/skirt and i finally tried one of my mom's dresses and ive been hooked ever since about 1 year later i started to try with bra's and thongs and her shoes to before my feet got to big.

I was five or six. The girls all got to go to halloween as princesses. I "got" to go as a hobo. . .

For me, my sisters pink nylon panties when I was 11.

I remember it well. I was twelve years old, and our junior high school was having homecoming. This included lots of activities, like a parade, and the football game, of course, and an "ugly" contest, where the contestants would try to make themselves as grotesque as possible. Good fun there, so I tried out. I knew a man who was in the theater, and he showed me stage makeup techniques. Nasty!

And I had an idea: I could cut flaps out of a pair of pantyhose, and it would look like the skin was falling off my legs. Ingenious! A sure winner. My mother told me that it didn't work that way, but what did she know? I was twelve, and I knew better than she! So I tried on a pair, tried to cut flaps in them, and ran them waist to toe.

Didn't work. I came in second place, and here I am, 36 years later, still wearing pantyhose....and a few assorted accessories. :battingeyelashes:

spose from what i remember a small child,4 maybe 5,was asked by doc if wanted to be boy or girl(wild child)wish id told the truth,maybe life would have been different,but wouldnt change what i am for the world.

i was about 12 or 13 at the time

I was 13 the first time I tried on my cousin's bra one summer when she was staying with us. I remember my reaction to it like it was yesterday, but the trill was followed by shame, guilt and all those negative emotions.

I didn't have the inclination towards repeating the behavior until 23, last year. Fueled by courage I worked up reading posts here, I went out and bought my own stuff at a TG specialty shop a couple months before I turned 24. Same thrill, just significantly less on the ensuing negative emotions roller-coaster. And that roller coaster ride gets lamer every time I ride it. :)

At age 11 or 12, and it was as simple as walking in to mums wardrobe and ....... well it's not really that much of a stretch to guess the rest.

It wasn't until 16 until I bought my first girl clothes. As soon as I had a few $$$ from a part time job it was off to KMart for a denim mini skirt and pink crop top, which seemed to be the teen fashion at the time. Oh happy days :daydreaming:

Tash :)

Occasional pantyhose in high school. Really didnt hit me hard all-out until 22 when I started buying clothes/bathing suits, etc.

i was 22, visiting my sister in chicago. she had left the sexiest pair of calvin klein panties in the bathroom. i slipped them on and i felt like one of those cartoon super heroes as the surge of satisfaction came over me. not sure why i started as i entered adulthood, but wish i had started sooner.

I was 12 or 13. I had the desire long before that, but never acted on it.

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Originally Posted by AKKaren

[SIZE="3"][/SIZE]I was dressing at an early age, I suppose...Sister's and Mom's undies and slips, shoes,stockings and jewelry. Boy, was I ever the depressed child. I felt nothing but shame, especially after everyone in my family found out. My Mom was horrified and beat me when she found me one day dressed. I still vividly remember that day:sad:

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Sorry to hear about what happened. But that is a great picture! You were really cute!

for me it was at the age of 4,, always from being born I was a cd,, I snuck into my sisters draw and stole a pair of her peach(yellow) silk panties,,she is 2 years older than me,, I kept them panties for 3 days,, on the 3rd day I had them on and there was a ruckus in my sisters room,,mom and her was ripping the room apart looking for them same panties,,guess sis loved them and was having a fit wanting them,,well I ran to my room and took them off and brought them to them and said the cat had them playing with them under my bed,,,yes a lame excuse but I was only 4 so they might of believed it,,well nothing was ever said about it since,,,,, growing up I have always at every chance wore moms and sis's clothes,,if I was home alone I would run to both of their rooms and gather my favorite things and put it all on,,, always scared that I would put the things away in the wrong places,, always took a mental note how the articles were layed and folded and looked for booby traps like a hair or a string because I thought they might have a clue and wanted to know for sure so they would set a trap,,,never found a trap but did always leave things just like I found them,,,for example the top panty draw wasnt shut all the way,,cracked open just a little,,

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Originally Posted by PinkCDgirl34B

One of my favorite questions!

fascinated with the Sear's and Penney's catalogues. You can guess which sections.
I still love to be in pantyhose, panties, Maidenform bras, vintage slips, vintage nighties, heels and all matter of fun femme finery.

Lacey

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That's what started it here too.... Oh my! Those bra's, foundations, garters and girdles!.... And then I found that "dirty" magazine in the ditch while walking home from 5th grade. (But that was a whole 'nother plateau of obsession for me.)

I was eleven or twelve, I 'borrowed' some panties from a friends sister. I lived in them lol, I'd wear them, wash them everyfew nights in the sink and wear them again.

My older sister and her friends would dress me up as a girl and we'd play school when I was about 5 or 6. I was never very happy about doing that, but at the age of 8 or 9, I discovered her pantyhose, and the rest is history.

I was 13 when I first started to experiment with crossdressing. I found a pair of white pantyhose and in the storage room of my parents house, I found a large box containing old clothes my sisters no longer wore. And for many weekends I would wear the pantyhose with whatever dress or skirt ensemble that was in the box. Took a long time before I finally began to wear heels and all the other stuff.
-Audrey

i was ten and i've always been in the closet but have always dressed regularly.i can't live without it :)

5 Decades ago when I was 7.. Sigh...

I was 8 or 9, helping out at a rummage sale......... Found a box full of heavy satin lingerie, slips bras & panties... Was hooked forever

Must be something funny that happens inside a lad of 8 or 9. For me I became curious about what it would feel like to be in girls skintight dancewear. So at age 10 while home alone, I sneaked into my sister's dance bag and put on her leotards and tights that she wore to dance classes and minced about the house in them. Been hooked ever since. Many years later, still love the look on the ladies and feel of them on me.

my first memory of crossdressing was probably age 11 I went into my sister's room and tried on her tan pantyhose and a dress and totally feel in love with the way i looked and felt standing in front of her mirror looking so pretty and cute since then i've developed into a beatiful woman :)

While me earliest memories are when I was around age 6 or 7, it was not until I was around age 10 that I had the best memories of my friend's older sister's lingerie. She was my size and would always hang her lingerie in the bathroom or laundry room. My favorite was her matching light blue bra and matching panties. I can still remember both the bra and panties had a little pink rose on them...they were my favorites. But, she had so many great sets, it was great growing up in my friend's household!

About age four found a slip in a box of clothes destined for the attic. I put it on and crawled into bed and fell asleep. Later when Mom came to tuck me in for the night, she found me still wearing the slip.
After that she told EVERYONE- grandmother, aunts, neighbors,etc., especially if she knew I was in earshot. I think she thought she could shame me out of ever wearing girl's clothes again!
I think her plan worked wonderfully well, don't you, ladies?:)

I think I was around 7 or 8, and it started with my Mom's heels.........and progressed from there. I got caught several times over the next few years, but eventually got better at hiding my "girly" side.

I was in my young teens i would wear my moms bras and hose and one of her dresses that i liked :D

[SIZE="3"]I started four years at age 56. Never had urge before then.

Gennee[/SIZE]

One of my earliest memories is my brothers and I all taking turns wearing Mom's heels....I first fully dressed, makeup and all, when I was around 10.

I would wait until a day where Mom and Dad were off doing stuff... and I would get dressed up in one of my Mom's outfits, undies, makeup, did my hair in a little short girly style with bangs, and wait for my younger brother(1 1/2 year difference) to wake up for the surprise!For me, there wasn't one item, like heels, or hose, but I wanted to try it all. I wanted to wear what all the girls my age would wear.

I ended up doing that quite a few times,now that I think of it...I was really sad when I started to outgrow my Mom's stuff...:(

i think i answered one of these threads before. My first desire was at 13. I was left all alone and started to explore my Mom's drawers and closets. She was the type of person who would get her hair done once a week and then if for some reason she didn't she had this wig that looked like her hair ( a somber red color, but not really long)

So it was never any one piece of clothing but it all! I did the bra, panties + a girdle. I was the perfect size to fit in all of this including the boots with the little heels. I would do my dress up every once in a while thoroughly enjoying it.

One day i was lamenting the fact my mom didn't have pierced ears. So i went out and bought a pair , sterilized them with a flame and alcohol and wore them for my dressed time. Never had a problem btw so anyone that is squeamish better take heed.

So i was pleased with myself and one day decided my brows were too bushy so unfortunately i took a shaver to them. Before i knew it i had gotten rid of my brows and i looked bizarre. I tried to draw them in with an eyebrow pencil but it was strange. It was ruthless from the kids in 8th grade and i quit crossdressing for like another 20 years. My parents didn't necessarily put it all together but told me i was very strange. BTW did you know the ancient Egyptians shaved their eyebrows when their cats died?

I've been dressing in a way since preschool.. more by the time I was in junior high and still more by the time I was in high school.. and of course I dress a lot now.. with age comes??....

This has been brought up before. From what I remember from previous threads, it seems like the responses this time are generally earlier in life than previous threads. It is always fun to read how and when people discovered their feminine side.

I started when I was 4 or 5. I had a pretty unique opportunity to dress up. From early childhood up until I was a teenager, my Dad was the "display manager" in a couple of different department stores. He had to go in nights and weekends to dress the manequins and arrange the in-store and window displays. Some times I would go with him. While he would be dressing manequins in one part of the store, I would be dressing myself in another. I remember I got caught once when my Mom showed up unexpectadly. I don't think she told my Dad but she was pretty upset and told me to get out of "those" clothes immediately.

I had the desire, but not the opportunity, in the 5 and 6 year old range. Without a sister or close cousin to borrow from, I was pretty much out of luck until my early teens when I was big enough for mom's things and was being left alone long enough to give it a try. I was in High School when I finally had my first chance to dress up all the way to makeup.

I was about 6. It was a pair of my Mom's black undies. This was back in the days when Moms could the kids alone for a few minutes to run next door for a 2 hour cup of coffee with a neighbor.

The movie on TV was The Creature from the Black Lagoon(still, in my mind, the most sexual(?) of the old monster films)...And there was just something about the scene where the woman was doing the backstroke, and the Creature was following below in syncronization.

That was about it, until 13 or so, when I discovered the joys of having access to my older sisters laundry basket & closet:heehee:

Bobbi

I started to wear girls clothes when I was around 5 years old.

Probably when I was 4 or 5. My mother once let me play "dress-up" about then, after that, I got into her clothes whenever I could. I've always been fascinated with women's clothes -- now more than ever!

It was 1963 and I was 12 and in junior high school at the time. The very first thing that I remember trying on was my mom's one piece swim suit...a very pale shade of green as I recall. Then I tried on my mom's bra, girdle, stockings, and high heels and looked at myself in her full length mirror...and the rest, as they say, is history.

for me i was about seven i saw this fullslip hanging on a laundry line and for some weird reason i just had to try it on and from then on patricia evolved:battingeyelashes:

I started at 5 or 6 with my mother's panties. It wasn't until early teens that I really got serious. There has been a few dry spells where I denied the urges over the years. I think now is the most active I've ever been.

When I was 5 or 6, I didn't have any boys my age in the neighborhood, so I played with my sister & her friends. It was all girls games including dressup. Dressing up seemed like th most natural thing to do & I never stopped from that point on. It got more sexual when I resched puberty. I do not regret it at all.

i started when i was i the 6th grade. i saw my mother getting dressed through a cracked bedroom door. She was putting her bra on. and i was hooked ( noun intended) lol. from then on i took every oportunity to go through her dresser drawers and try on her things:heehee:

I was in my early teens and home alone. For some reason I tried on a pair of my Mother's nylons and i was hooked. Loved the feeling and the rush it gave me. I put on one of her girdles and hooked them up under my jeans. I played with dressing off and on after that but didn't get more serious about it until after my divorce - my gf and I went out for Haloween dressed as "each other". I dressed in panties and bra skirt and top. I loved shopping for the clothes and accessories and loved the feeling of wearing a skirt. I still love the feeling. I don't want to be a girl - what they have to go through would be a nightmare for me but they do get to wear all the cool stuff.

My sisters started dressing me when I was young. I was just one of the girls. The first time I dressed myself was around 8. I stole a pair of my sister's panties, a dress, a headband and clip-on earrings.

A couple of my cousins dressed me up in panties, tights and a dress when I was 7. I protested, but it felt so right. After that I just wanted to continue doing it. Bought my first bra when I was 13 and have never looked back.

When I was very young my mother would have me dress in my sister's panties whenever my boy undies were dirty. That seemed to happen a lot. When I was older I realized that there was a 7 year difference in our age which led me to believe I actually had 'my own' panties. I would often be dressed in a girl's T-shirt also and I think socks. At the time most girls wore nylon panties. I soooo... rermember that! My mother also used me for a dress model for a cousin that was my age. When I was eleven I dressed up as a colonial girl for Halloween. Didn't think anything of it. It was just a costume. Then I heard a conversation awhile later about not wearing pants under girl's skirts. I started thinking to myself that I had worn pants under my Halloween costume. As a lark I wanted to know what it was like to not have pants on under my dress. So I did so. About that time I also saw a movie on TV during the civil war where the women were wearing corsets. I knew my sister had a corset so I tried that also. Curiosity got the best of me and I eventually tried on some of my sister's other clothing. It wasn't until I was wearing a girdle and nylons and a sheath skirt that I actually got erotic feelings. When that happened I was hooked for sure. Erotic feelings lasted for approximately ten years. Maybe as much as 15. I no longer dress for that kind of thrill and haven't for well over thirty years.

i was 10 and still doing it at 45