How did you start down this road?

[RichardTO]

I started just before my teenage years. Had a sister and two stepsisters who always seemed to get away with everything while I always seemed to get the short end of the stick. Complaining to them about it got nowhere, they always said "You don't know what it's like to be a girl!" and never argued anything further.

One night, I went to my mom and asked what it was like to be a girl. Her response was that it was just something you do. After a bit, she suggested for me to dress up to get an idea of what it was like and she put me in one of her dresses. I was told that with a little makeup and my hair done, I'd be a very pretty girl. I wanted to see, so next day we did that. That was the point mom said that I looked good enough dressed that maybe she should start getting me dresses and skirts. Was a bit taken aback, but she offered to buy me things if I would wear them. I kind of liked it, so I agreed to it.

That started several years of very regular dressing, both at home and outside. I left it behind when I went to college, but the memories are always there.

[bridget thronton]

My dressing was hidden from my mom while growing up and wearing her clothes.

[docrobbysherry]

I started in my 50's. Dad had passed and my mom had Alzheimers. My daughters disagree about Sherry, but my sister thot it was cool!:battingeyelashes:

[Cheryl T]

I was 5 or 6 when curiosity got me and I tried mom's panties. They felt so different and actually so right, I loved them.
Sometime later I tried her bra too and as time passed a slip, then a dress, an OBG and stockings, then her heels. When I dressed completely the first time it just felt natural.

[RichardTO]

Yeah, I wound up with panties, bras, nightgowns, swimsuit, a sundress, skirt and blouse almost right away (not to mention a couple pairs of shoes).

I don't know if I would have started without the help and encouragement of my mother. Being a kid it was hard to understand what her motivations might have been. Wasn't until I was talking to a therapist about it in my 30's that they pointed out that my mother hated my father after their divorce and I was a small version of him. Add to that mom was a raging narcissist, and it gets easier to see.

Not to say I didn't enjoy a lot of it, or that it didn't help me grow as a person.

[April Rose]

I remember having an interest as young as 4 or 5. I got caught a few times around age 7. It could have gone worse, but that doesn't mean it went well. The first time learned the word "transvestite" I knew that was who I was.

[Bluesman]

I was 15, playing one of the kid roles in a professional production of Macbeth. Dressing room space was limited, so couple of the gay men and me (go figure!) shared space with the female cast with just a clothes rack separating us. One night when I was alone in the dressing area, I noticed a pair of panties on a chair. I pocketed them, took them home, put them on and masturbated. Around that same time I discovered a trunk in the attic with a couple of nightgowns in it and started wearing one to bed. Over the next years I found or purloined panties until I got up the nerve to buy my own along with a matching bra in my early twenties. Dressing was limited to those kind of lingerie items, off and on, periodic purges, reading cross-dressing letters and stories in Penthouse Variations (how many remember that publication?) til my mid-30's when I bought my first dress, which was later purged. Things continued that way more or less for the next 20 or so years, hiding it for the most part from my wife. In my late fifties decided the only thing "wrong" with CDing was hiding it from her, so put it more out in the open. Didn't go well initially, went back into hiding although the secret was out of course. Eventually started purchasing dresses, skirts, blouses, shoes, etc. wearing them in private, and occasionally being caught if my wife came home unexpectedly. It's all out in the open now, and I dress more or less as I want to.

[LizMichelle]

Age 8, discovered a dress I liked at a second hand store. Mom noticed I liked it, with me having Asperger's Syndrome and let me try it on. Went into the dressing room and put it on and loved it on the spot. Came home with it, mom did buy it for me.

[oh to be rachel]

There was always a tickle of an interest.
It was a neighborhood costume party where the wife and I wore wedding dresses that set it on fire in my head.
Years of pink fog followed.

[NancySue]

At 5 or 6, got invited to play games by next door sisters. After a couple games, they decided to play dress up and invited me to join them. Initially, no interest, until I tried on some thigh highs even though they had runs. Wham, bam. ⚡️ They felt so good. Still do. The sojourn began.

[BLUE ORCHID]

It was 78 tyears ago @ age 4 Playing with Mom's Hose & Heels, And the Rest is History,

[sara66]

Around 4 or 5 put on one of mom's bras and progressed from there,
Sara

[Georgina]

It started with me in the late fifties (1950s) when I saw my first petticoats and stockings and suspenders at school. I began by wearing my mother's and much later when I got my own clothes it felt wonderful and right. I have continued dressing ever since.

[CarlaWestin]

Mom's bras.

[Erin77]

Around age 5. Moms panties. Don't know why but the material and feel of it just kept me going. Then bras, lingerie, pantyhose and finally just dressing all up as I got older.

[countrygirl]

Started at age 11 with moms bra and panties and then quickly added moms skirts and blouses and into dresses. At grandma's house wore some old wigs she had in a trunk and one of her dresses in the bedroom that I stayed in and next thing you know it took off from there. Now 44 and living on my own and have more female clothes than male and looking at microdosing HRT and loving every minute of being able to express this side of me. Who knows what is next maybe it is transitioning to female. Don't know and frankly don't care to know. I know that I can express this side of me and love every minute of it. To be able to express this side I that was not allowed to flourish and enjoy and now I have the freedom to do so. I love it.

[Sabine Janus]

Sister dressed me as her doll.

It took.

[Monique65]

I found my mother’s OBG and stockings, slipped them on, and my world changed.

[Jillcder]

When I was in grade school I dressed as a girl for the school Halloween party obviously I did not resist and I can still remember my teacher telling me my makeup looked good. Not sure if that seal the deal on my Crossdressing journey but it is my earliest memory.

[JesseVF]

Very young but I think it was actually open bottom girdles I found in the laundry. Soon after that Moms bras stuffed with whatever I could find.
I?m jealous of those who were assisted in this pursuit. I remember putting on a dress over my clothes once when hanging out with my older sister trying to get her to take the hint but she pretty much ignored me.
And yes Bluesman I remember reading the Penthouse letters and always hoping there were more of the cd examples. Newspaper advice columns also once in a while included a cd example which of course I found fascinating.

[Stephj]

When I was young about 4 or 5 when I would go to the store with my mom and sister she is three years older than me they would find me in the lingerie section of the store looking at and feeling the panties and bras. Then one day i was at home I walked by sister?s room and on her bed was a folded bras and panties she had just laundered. I went in to feel and look at them time got away from me. Next thing I new my sister was in the doorway she said would you like to try them on I said yes she have a pair of panties and go try them on them she help me with the bra I was hooked. I wore them every day. Then about a month later mom have me a hug and realized I was wearing a bra she said boys don?t wear bras for sister said he is also wearing panties had to take them off. A week later I asked my sister for them she handed them to me i started wearing them again about a week later mom found out she finally said I figured s you like them from all the times i found you in the store looking at and feeling them. She asked if I wanted my own I said yes. She said I would have to buy my own. I had allowance money I had saved so we went to the store I bought two pairs of panties black and blue along with two bras. Been wearing them ever since. I will be 61 in a few months

[Stephanie47]

The very first time I ever put a femme garment on was my mother's nylon nightgown. I know I was very very young. My mother constantly was saying I was suppose to be a girl because her first born was a son. He is a year older than I. I guess her idea of the perfect family was husband, wife, older son and younger daughter. I put the nightgown on and cried that she did not love me because I wasn't a girl. She hugged me a told me she loved me and never said anything about me not being a daughter. I often wonder if that set my mind on the direction of wanting to wear femme garments. I always believed that my mother doled out more physical discipline for me because I was not a girl. My older brother walked on water and got all the new toys/bikes while I got my ass whipped. A couple of years later I discovered her full slips that she hanged to dry in the hallway leading to the bedrooms and a drying rack over the bathroom tub. I loved the feel of the nylon. At first I just fondled the slips but ultimately I had to slip into them when I had the chance. I had an experience as a really younger kid, maybe four years old.

When I was about four years old I started having visions that I was a young woman who had been murdered and left in a muddy dirt parking lot and I was dressed only in a white full slip. I have no idea why this vision arose because we did not have a television set and I know nobody would have been talking about something like a murder with that much visual detail. It wasn't until decades later than my wife started watching a program concerning "past lives" that children remember that, just maybe that was such an experience.

[Katherine L.]

I first started at 11 or 12 by wearing my mom’s bra I found in the clothes hamper. Now almost 67 and I still love wearing bras.

[Kelli_cd]

I used to spend summers living with my grandparents. When I was 4, I discovered my grandmother's petticoats. I only ever write them over my clothes, but i liked them.
When I was 7,I tried on my mom's girdle. I didn't care much for that. I remember it feeling very rubbery. (It's odd, now i would love to have a girdle! )
At 11 or 12, my mom and sister both started wearing nylon panties. After wearing their panties, there was no turning back.

[KrissyTN]

I was around 7 when I started to notice my mom's bra's on a stack of towels just above the clothes hamper. Being in the bathroom like that afforded me the opportunity to try it on one day boom, I was hooked! After that, whenever I had the chance I would try on various clothes. It wasn't long before I discovered that my aunt & grandmother wore OBG's with garters and that set me down the path of admiring and loving those, garterbelts and stockings. Heels were much later, but a fun discovery too!

[cdinmd206]

Ever since I can remember I had a love of lingerie. When I was 7 or 8 the girl who lives across the street had a birthday party and one of her gifts was a package of nylon panties with the days of the week on them. I was admiring them and my mom asked if I liked them and I said yes. She then asked if I would wear them and I again said yes. Two days later she gave me my own day of the week panties. Unfortunately when my dad found out and that was the end of my panties plus a sore back end.

About a year later I was spending some time with an aunt who always wore a dress with stockings and heels. As I walked by her bedroom, the door was slightly open, and I peaked in. OMG I will never forget the sight of her removing her dress and slip. Underneath she had on white see thru frilly panties, white garter belt and a very lacy bra. Later that day I went into her bedroom and was looking thru her Chester drawers checking out her lingerie. I was holding a pair of her frilly panties when she walked in. I just knew she was going to whip my butt and tell my parents. She calmly told me to put her panties away and then asked why I was in her bedroom. I told her I had seen her changing clothes earlier and was fascinated by her lingerie. She told me it was wrong to go snooping around like that and to not do it again and she would not tell my parents.

About a month later my aunt asked my parents if I could spend the weekend with her to help with some yard work. I was dropped off Friday evening and Saturday I spent all day doing yard work. That evening my aunt told me take bath and when I walked into the bedroom in my robe my aunt was sitting on the bed and on the bed was some lingerie. My aunt said these are for you to wear inside my house and it will be our secret. I turned my back and slid on a pair of nylon panties. When I turned around my aunt was holding a training bra ad she fastened it on me. She then hooked the garter belt on me and when she slid those stockings up my leg and attached the garters to the stockings, I knew I was hooked on the feeling. She also bought me a very frilly dress. She said now you are my niece not my nephew and again it is our secret.

Up until I was 16 I would spend many summer days at her house. My parents thought it was a great idea to be helping my poor widowed aunt with all the yard work and upkeep to her house!!!!!

[GraceH]

My second grade teacher used to punish boys for misbehavior by making them wear a headscarf for the rest of the day, including outdoors at recess. I never received that punishment, but wanted to. So, one day, age 7, I put on one of my mom's scarves and headed out into the back yard, where I was seen by a neighbor. I never heard anything more about that, and it didn't daunt my curious explorations into my mom's stuff. The first time I put on lipstick, still age 7, I recall a huge rush of excitement, carried away by the feel, the fragrance and the appearance. I regularly wore her skirts and bras, and wasn't caught as far as I know. I know my dad would have violently disapproved, so I had to keep it hidden. After college, I acquired a full wardrobe, and except for a couple of purges that didn't last long, I've been dressing regularly ever since, 70 years total from that 2nd grade exploration.

[SaraLin]

I've always - ALWAYS knows I should have been a girl, so I took every chance I got to try to look the part.

Even as young as 4-5, I'd sneak something of my sister's to wear in secret. I also raided my grandmother's attic for some old outfits I found in boxes up there. I "liberated" some of these and took them to my "hideout" in the woods out back of our house.

But unlike so many others, I was less fascinated by the underthings. I wanted to LOOK like a girl and that meant that the outer things were what was important to me. Dresses, skirts, and tops were my thing. Panties and slips soon followed, simply because it was what a girl was supposed to be wearing underneath. It was only as I got older and the girls my age started developing their figures that I started thinking I needed to wear bras. Again, it was more to achieve the look (boobs) than any erotic element. Hose, girdles, etc. - same story.

[Giselle(Oshawa)]

Around age 10 or 11 yrs old, my parents were out and i went through my mothers lingerie door.
Before I knew it i had on one of her bra's, an obg(girdle) and nylons.
I did this for probably 2 or 3 months and I am certain my mother suspected.
She bought me a dress for Halloween( inside I knew she knew) I refused to
try it on and never raided my mothers drawers ever again.
If only i had tried it on maybe my mother and I could have had THE TALK?
I have regretted not trying on that dress ever since.

[Liz Jones]

Wife told me to put my name down for a ( men only ) beauty contest, i ended up dressed in leggings & a summer frock -- in the middle of a Scottish farmers field . This started the " itch " for which their is no known cure.......

[DanielleDubois]

I'm sure in different thread I have said it all started for me at age 10 or 11 when I found a corset style girdle and a mohair sweter dress in a cedar chest in the basement of my parents house. Why those two items were the only things in the chest besides some old documents I have no idea. But I tried them on and found out I really enjoyed the look and feel. Never felt I was meant to be a girl but from that point on I enjoyed occasionally becoming one or at least looking like one.:)

[Lacey New]

Sometime in my early teens, I started to notice girls and the bumps on their chests and the bras under their blouses. Also, in the age of short skirts, offered a glimpse of panties now and then. Then there were the JC Penny and Sears catalogs that had many wonderful color pictures of women wearing bras, panties, slips and other pretty lingerie. As a young boy, I was fascinated with what could be underneath. Well, one day, home alone, I spied a pair of nylon briefs hanging out of the common clothes hamper. They were either my mothers or my sisters but they looked and felt soft and silky and I just had to try them on. You can probably guess what happened and you would be correct. I felt guilty and that maybe I was gay or somehow perverted and I vowed to never do it again . Until a few days later, I had another opportunity and did it again. From that point on, I would put on panties and ultimately bras and slips whenever I could. Eventually, when I got out of college and out in my own apartment, I acquired my own large collection of lingerie and some outerwear

[Debbie Denier]

Trying on my mums tights aged 10 or 11 was a game changer for me.

[Lacey New]

Very young but I think it was actually open bottom girdles I found in the laundry. Soon after that Moms bras stuffed with whatever I could find.
I?m jealous of those who were assisted in this pursuit. I remember putting on a dress over my clothes once when hanging out with my older sister trying to get her to take the hint but she pretty much ignored me.
And yes Bluesman I remember reading the Penthouse letters and always hoping there were more of the cd examples. Newspaper advice columns also once in a while included a cd example which of course I found fascinating.

I used to look for the ads for Michael Salems TV Boutique

[Raychel]

When I was young, My bedroom was next to the laundry.
With my mother and 2 sisters in the house, I had access to
many items that had been thru the laundry and on the folding table.
One time on a whim, I tried on a Girdle and other panties.
The rest is history :) :) :)

One thing leads to another..............
To where I am at today, :)

[KrissyTN]

<I used to look for the ads for Michael Salems TV Boutique>

I remember Michael Salems, Lacey! Seems to me I sent away for one of their catalogs once upon a time. I had to first get a PO Box so it didn't show up and arouse family suspicion.

I love the pen & ink drawings from those ads and I saw some work from the artist not too long ago on FB. Brought back some memories for sure!

Krissy

[Maid_Marion]

As I was approaching fifty my wife was worried about me getting laid off my job, so we watched What Not to Wear.
Problem was that I was too small to wear men's clothes.
Not only that, but we didn't know yet that she had ALS so her hands no longer worked well enough for altering clothes.
The solution was wearing women's clothes, primarily J. Crew tops purchased on eBay. Back when they were of higher quality.

[BobbiKay]

As a young'un I remember trying on my grandmother's heels. They didn't fit, of course, and I was told to stop that stuff immediately.
As a (pre?) adolescent, I would try on my mother's drawers, girdles, and hose.
There was the Spencer's and Sears catalogs -- many definitions of "the wish book"!
When I was on my own, Variations was a frequent purchase.
I switched from flyfront tighty-whities to Jockey "Elance", which as far as I can tell are unisex (but the ones in the men's department don't have a numeric size, just s/m/l).
I would sometimes "borrow" my (now) ex's pantyhose to wear under my suit to the office, and wear her leotards around the apartment.
Along the way there was a girl that I was attracted to, who was of similar stature and build to me. I remember thinking what fun it would be to share clothes with her. But alas, the relationship remained platonic.
In the last 10 years or so my dressing has taken a decided turn, ever since I discovered the joys of thrift (and thrift-store outlet) shopping, which doesn't break the bank.

[jjjjohanne]

I am not sure, but the first thing I may have ever tried on was Barbie's panties. I put them on my big toe and I felt good. I fantasized about wearing a slip. I loved silky fabric. One day I tried on a slip. Eventually, I tried on pantyhose. They made everything feel like a slip. My mom had used some old stockings to tie up tomato plants one year. I saw them in the winter and untied them and kept them. The sun had bleached away the suntan color and left them looking tie-dyed. I found some old pantyhose that my mom had left in a storage room drawer for use to store onions or whatever. Those were "Silkies" brand. They had the sparkly panty section. I loved the sparkles! Eventually, I became old enough to be left at home and I started trying on whole outfits of hers or my sister's. For a while, I could move her slingbacks to the last hole and I could wear her shoes. But, that passed quickly as I grew.
I was out of college, driving home from work, when I got the idea to go to the store to buy some pantyhose. That was SOOOO scary. I bought $30 worth of groceries to mask the hosiery purchase. That was the first pair of new, pristine pantyhose. Eventually, I went to a dollar store and bought some panties. It wasn't until I moved out of my parent's house and got married that I acquired other garments. I still remember how it felt to go out in public in all women's clothing (but looked like menswear) and screaming inside, "I'm in all womenswear!!"
Eventually, I started going out for morning walks in womenswear including shorts and nude pantyhose. One day, I wore a sport skirt that had shorts built into it. I pulled up the skirt when I was around people and they couldn't tell. At some point, I did not realize someone was near and I the skirt was hanging down. The world did not end.
The next day, I wore the skirt, but did not pull it up. I just wore it in front of people. That progressed to me wearing a normal skirt on my morning walks. I passed some people and they said "hi". Nothing happened. Eventually, I realized that I could just wear women's clothing and present male and it did not matter.
Many years went by and I started owning clothes that actually make me feel pretty. I wore some rather atrocious outfits over the years!

[alwayshave]

I had been dressed in my sisters hand me downs, but the first thing I remember that was of my own accord was my mother's Merry Widow. That item was stored on the attic stairs which were located in my bed room.

[Christina89]

I remember I was about 12 years old when I discovered the "pre-teen" girl in me. I was home alone one day after school watching tv, I was watching a show called Totally Spies. The main characters were out and about buying clothes for themselves. As I was watching an old memory popped in my mind where I asked my mother why I couldn't buy some of the clothes the girls were picking out for back to school. I grew up with what we all call an extended family and at the time the family had 2 daughters. 1 was about 3 years older than me and the other was about 2 years younger than me. My mother told me I couldn't cause they were girls clothes and deep inside I was deeply disappointed cause I liked the way they looked. Fast forward back to watching Totally Spies and something awoken inside me. Without missing a beat I went upstairs to my mother's room and started looking around. I found one of her bikinis on top of a box going into storage for the fall and winter. I decided to start with those. I took them and went into my room since it was in the back of the apartment and away from the street, the street we lived on was the main road into our neighborhood. I started to strip down and as I was putting on the bottoms I felt the awaken getting stronger. Then I put on the top and tied it up and the awaken came fully out. Afterwards I went to the bathroom and checked myself out in the mirror. I loved the feel of it on my body and had to admit my male breast looked amazing in the bikini top. After seeing myself for a few minutes in the mirror I went back to my mother's room and found a skirt, bra and top in her room and grabbed them. I returned to my room, took of the bikini top and put the bra on. I didn't struggle cause for a short period of time when I was 5 or 6 my mother and I lived in a one bedroom apartment and at times I saw her put the bra on while waking up. After putting on the bra I put the skirt and top on. I returned to the bathroom and saw Christina looking back at me with a smile on.

[Lori Anne]

I was about 13yo, read an article in Playboy magazine, where a man had been put in panties, before sex; stole a pair of my sister's panties, and acted out the article. Years later, the sexual part of the equation had left, and I just started to feel more normal being at least underdressed.

[Teri Ray]

Well I hope this information will not become shocking to others............ but I too found my curiosity to try on my mothers things at a young age (I know quite different right?). I can't recall with absolute certainty but I figure I was around 6-8 years old. Found an old bra in the rag bin and tried it on. I liked it and soon found myself looking in my mothers dresser for panties and stockings. Gosh I found liked them a lot too (guilt sets in) I have been hooked ever since.

Does this mean I am a crossdresser?

[Snide_lobster]

Yeah, I wound up with panties, bras, nightgowns, swimsuit, a sundress, skirt and blouse almost right away (not to mention a couple pairs of shoes).

I don't know if I would have started without the help and encouragement of my mother. Being a kid it was hard to understand what her motivations might have been. Wasn't until I was talking to a therapist about it in my 30's that they pointed out that my mother hated my father after their divorce and I was a small version of him. Add to that mom was a raging narcissist, and it gets easier to see.

Not to say I didn't enjoy a lot of it, or that it didn't help me grow as a person.

I?m confused, the actions you describe just sound supportive, if perhaps not a little on the strong side, but far from immediately manipulative or narcissistic? I fail to see how your therapist comes to that conclusion about this aspect of your relationship. Obviously we only have a snippet here, and I?m not trying to pry, but do you feel that she was purposefully trying to emasculate you, because it sounds like you were exploring something you wanted to explore? Did the relationship change over time, become forceful or transactional, or was too encouraging/imposing her will on you? Idk, from the actions you?ve written it just seems like she let you dress up as a girl.

[AlicePetticoat]

I tried on pantyhose that belonged to my mother when I was in my teens. That rush when I slipped the nylon onto my legs made me more curious. I ordered my first petticoat a couple years later, and the rest is history.

[RichardTO]

I?m confused, the actions you describe just sound supportive, if perhaps not a little on the strong side, but far from immediately manipulative or narcissistic? I fail to see how your therapist comes to that conclusion about this aspect of your relationship. Obviously we only have a snippet here, and I?m not trying to pry, but do you feel that she was purposefully trying to emasculate you, because it sounds like you were exploring something you wanted to explore? Did the relationship change over time, become forceful or transactional, or was too encouraging/imposing her will on you? Idk, from the actions you?ve written it just seems like she let you dress up as a girl.

At first, it was just her letting me dress up as a girl, yes. It didn't take long for her to start pushing me to dress regularly, and it was made clear to me that this wasn't just something I got to do at home. Things like the first Christmas after I started, mom was choosing clothes for us to wear for dinner with extended family (she always chose them to look nicest for family photos) and she pulled out a blouse and skirt for me. I didn't necessarily want the extended family to know about it, but I was told I had no choice. I wasn't going to fight mom on it, I had learned growing up that she always got her way or life would be miserable. It certainly didn't help that my stepfather backed her up all the time.

I spent six years dressing regularly, and she pressured me to do it as much as possible, even pushing for me to transition to living as a girl full time when we moved across the state when I was 16 (I fought back and didn't). There was a lot of emotional manipulation in there--she would be affectionate and supportive of me anytime I was dressed, and dismissive and cold when I wasn't. I was punished for doing anything she deemed to be too much like my father and rewarded for being more feminine. I seriously cut back on dressing when I moved out and went to college because I didn't have a strong desire to do so.

There's a lot of stories I have that highlight just how narcissistic my mother was in other ways as well, how she tried hard to mold me into what she wanted me to be.

[Snide_lobster]

Yeah that?s horribly manipulative, sorry you had to go through all that.

[Petra1]

Honestly? When I was in seventh or eighth grade, I wanted to see what it would be like to have boobs.

[RichardTO]

Yeah that?s horribly manipulative, sorry you had to go through all that.
Yeah, this is the woman who, when she didn't get to have my kids visit her for their birthdays (because they always spent them with their mother and I), threatened to sue me for every penny I had. Then a couple weeks later when I calmed down enough to call her and try to work things out, she said, "I'm sorry I ever gave birth to you."

With all that said, I've tried to use my experiences to be a better person. Getting an idea of what it's like to live on the other side gave me a lot more empathy for my wife and women in general. I'm much more a champion of LGBTQIA+ issues and rights because of how nasty some people can be towards them just for existing.

[MsEva]

as others have said, the first truly fem items that I can remember dressing in was two Merry Widow Corsolettes that were left in a trunk in our attic by the previous owner. I think that was around the age of 15 but I always was attracted to fem items. I think that I tried on Mom's girgles and bras but not really clear on that timing. When I found the corsolettes I was in heaven. I had them for many years and would dress in the bathroom as often as I could.

[Bruce64]

For me it was an accident

[CynthiaD]

I?ve told my story several times but I enjoy telling it so here goes. I started at age 3 when I begged my mother to paint my fingernails red. I showed the other kids in the neighborhood and they told me that only girls wore nail polish. I didn?t care. I asked my mother if I could wear perfume, and she showed me how to apply it. I secretly started borrowing her clothes and wearing them. I continued wearing nail polish. My mother was out socializing with friends a lot and my father was only home on weekends. I was left home to baby sit my younger siblings. I would put them to bed and use the remaining time for dressing up. By the time I was in 6th or 7th grade I was fully dressing with bra, panties, full slip and a dress. I got caught with my mother?s clothes a couple times during this period. I made lame excuses that were probably not believed. I think that my parents knew but were too embarrassed to say anything. I found my father?s stash of feminine undergarments once. That?s probably the reason he never talked to me about it. When I was a junior in high school I decided to give up the girl stuff and learn to be just like the other boys. This was pretty much a disaster but I don?t want to go into that here. I promised myself that I would never even think about female clothing ever again. I stopped dressing, but never stopped thinking about it. I looked at catalogs and fantasized a lot. I finally couldn?t stand it anymore. I accepted that I was a crossdresser, and started dressing again. I?ve never been happier.

[Sabine7]

I think, in my case, everything started with an unconscious desperate attempts to clarify my real gender identification. As a toddler, I had a very pleasant and satisfying dream, so good that I still remember it. I was a naked female in high-heels publicly on a stage... Next, when I was less than twenty, I was lying down on a coach one day and came to a clear conclusion that I would have been much more satisfied if had been born as a girl. This idea is still with me all the time.

[krissy]

i was about 8 or ten i traded clothes with my sister at a movie house ill never forget that feeling of coming down the stairs. i felt like a queen, i felt like the prettiest girl there

[Lana Mae]

It all started with a little girl named Lana! She was flipping her white dress over her head and giggling! I wanted a dress! And so it began...
Hugs Lana Mae

[jacques]

hello Richard,
when I was young I wanted to dress like my hero Robin Hood so I tried on a pair of my sister's tights...
Luv J

[Mercedes]

I don’t know. Since I was 10 or 11 I wanted to wear women’s underwear. Not having any sisters I tried on my mom’s bra and just knew. By the time I was 14 had some of my own panties that I liberated from a store.

[abby054]

It started at age five when I saw the sister of a friend all dolled up. This was in a long gone time and place when mothers dressed their little girls is frills, ribbons, and bows. I wanted to look that good. I investigated the possibility but I did not like the answers, also products of the same long gone time and place. Nonetheless, I found fleeting occasions to dress, such as Halloween and after work. I worked as a janitor in a small church with a clothes lending closet.

[susan2010]

4 or 5. My sister's petticoat called to me. I had to see how it would feel to wear something like that. Later, mom's slips. Over 60 years later I have a large collection of my own.

[Lauren Richards]

Innocent curiosity..

[HollyGreene]

When I was about 4 all the kids in the street were boys. I don't think I'd ever seen a girl.
Then a new family moved into the street and they had a daughter. When I first saw her I was in awe. She was wearing a pretty dress and I wished I could be like her.
Shortly afterwards my sister was born and several years later I tried on some of her panties, and I was hooked. As we grew up into our teens, there were a few of her skirts and dresses that fit me and I wore them regularly (without her knowledge).
I used to do a newspaper delivery route. On Sundays the papers were big and heavy so I used to use a closed cart to carry them. One Sunday, one of my customers had put out a large bag of clothes for goodwill. Knowing the family had 3 daughters around my age - one of whom I knew at school. I figured that there might be something of interest in there. As you can guess, the bag ended up in my cart and I finished my deliveries wondering what was in there.
As this was very early morning, I got home before the rest of the family had got up and I was able to get the bag up to my room.
I wasn't disappointed. All the clothes were teenage girl's including dresses, tops, a bright yellow swimming costume, and a couple of bras. Most of them fit me quite well so I wore them as often as I could.

Apologies to the goodwill people, but the clothes did go to a good home (in my opinion).

[LelaK]

When I was about 4, I asked my Mom if I'd be like her when I grow up. She said no, boys grow up as men, not women. I was disappointed, since I wanted to look like her, not like a man. I don't know if I thought about that any more. Maybe I was satisfied with my fate. I know I didn't want to be like my sisters though.

When I was 9 or 10 I was in a 4H play, a comedy about a sort of hillbilly wedding. My sister was the best man and I was the maid of honor. The 4H leader had a nice looking fancy dark green satin-like dress she let me borrow. It felt like heaven. I got to practice once or twice for the play and then actually be in it. The following year I made up a play myself in which I played a lady in a fine dress walking in the park past 2 men sitting on a park bench. One was a gentleman in a suit reading the paper. The other was a bum. I dropped my hanky for the gentleman, but he didn't notice. Instead, the bum picked it up and loudly blew his nose with it.

Around that time, my sister had a short green dress like a girlscout dress. One day I took it from her closet and put it on once or twice in the bathroom. Instead of putting it back in her closet, I stashed it under the upper bunk bed. One day Mom found it and when we got home from school she showed it to my sister and both of them then confronted me in my bedroom, Mom asking sternly why did you put her dress under the upper bunkbed. Somehow I quickly thought to say I wanted to see how long before she would notice it was missing. They were satisfied with that answer and didn't say any more about it. That made me very nervous.

I would say you were very lucky. I bet there are a lot more lucky girls these days than back in the 50s and 60s.

[Jane G]

So long ago now. I used to dream about being a girl from my earliest memories. I have only sisters and female cousins to relate to. I was always the only boy from my earliest years. We played together as a group of young people. I was simply one of the group. Never really realised I was not just one of the girls until junior school. By then it was too late. Being a girl was simply more fun. Alas my parents and society at that time didn't think the same, so it all went underground. Did me a favour in a way. I know now that I am just a man that was conditioned through fun and circumstance, to enjoy being a women. As a teenaged that was very confusing and I think some modern male tenagers transition when they should actualy stick it out and would enjoy later life more as crossdressing males. But we can each only deal with what we see in front of us.

[Natalie5004]

We had a female centric house when I was growing up. 3 older sisters, pretty domineering. I loved them and still do. I wanted to be one of them.

[AllieBellema]

It was in my teenage years. Of course, I'm beginning to discover who I am during these years. My grandma was watching some old time movies with women in these beautiful southern belle dresses (not sure if it was Gone With The Wind or some other movie when it happened... I do know that my grandma had GWTW on tape and I would watch the first hour or so just to see the dresses) and something clicked inside me saying that I want to wear something like that. Of course, I started looking things up on the internet and discovered cross dressing. Eventually, during Halloween one year... I got the courage to by a female costume and a wig at a K-Mart. Was a poodle skirt outfit.

It was about a year or two later that I got the courage to ask my grandpa about ordering a "halloween costume" online. Of course, it was going to be my first southern belle dress. Wasn't as spectacular as the ones I wear these days, but it was something. Wearing that and spending alone at home times diving into my grandma's clothes closet led me into crossdressing. Of course, they never found out about it as I was pretty good at hiding it. When I moved away, I closeted everything up for a few years. Left everything behind and started a new life. Many years later, I got back into it and I started to get some better stuff to wear.

[Elizabeth G]

I grew up in a mostly male household except for my mother (who ran a pretty tight ship). I had two brothers, no sisters and no close female relatives.

When I was about 11 and beginning to notice girls I turned to the only source of visual stimulation I could find in the house, the lingerie sections of the Sears and JC Penney catalogs (This was on the pre-internet days). After a while I realized that I was just as fascinated with what the models were wearing as I was with the models themselves. I wanted to wear what they were wearing. I wanted to look like them. I wanted to be them. I vividly remember wishing when I went to sleep at night that I would wake up in the morning and be a girl.

I still do.

[Diedre]

Around age 12/13 my mother used me as a dress dummy for sewing and alterations which I hated at first. Then when I started wearing some undergarments to make things fit better I went head over heels (no pun intended).

But then after I started showing too much interest in remaining in the girdle, bra etc. after the fitting was over, I got replaced buy a dress form from a second hand store. But by then I was hooked and never looked back.

[DanielleCD]

I was about 14 years old or so... out of curiosity, tried on my mom's pantyhose. It felt so nice. Then graduated to my younger sisters panties and bras and have been hooked ever since. Something just feels so right. To this day, just to go about the house in my own fem underwear, breast forms filling out my bra and a simple dress.. I just feel normal.

[Heather76]

I can't pinpoint my exact age, but I was around 11 or 12 the first time I put on one of my mom's bras. I loved wearing it. I also put on her slips. After age 15, I don't recall ever doing that again. I married at age 20. During a 17 year marriage, I put on my wife's pantyhose probably 5 or 6 times and that was it. Into my 2nd marriage, one day my wife told me (I was complaining about something) "to put on your big girl panties and deal with it." Two days later I purchased a 2 pack of big girl panties and I've been hooked ever since. That was slightly over 5 years ago. I turn 80 next month.

[~Joanne~]

It started with a pair of pantyhose. I always was amazed at the sheerness of them, how they made women's legs and feet look amazing. I thought it was just a fetish, or preference, how they followed the leg and moved with them perfectly. One day I decided to try them on because I had to know how they felt to be worn and there has been no turning back since, I seriously think that if there were no pantyhose any more that I would never dress again. It all starts with them and it ends with them.

[Lea]

In my case a combination of things.

My mom wanted a daughter. I was supposed to be that daughter but disappointed her. She would always tell me that she did not cut my hair and people thought I was a girl.

When my father was passing, I took a photo of my daughter along with other family pictures to his bedside. He looked at his grand daughters picture and said that was me in a dress. I said no it's my daughter. He told me that no it was me and mom used to dress me as a girl but stopped it completely when I went to school.

While in elementary school and middle school I would wear my mom's girdles, dresses and skirts. I was hooked.

When my mom was passing and in memory care, she confirmed the story dad told me.

In one aspect I have not progressed very far. I am still wearing girdles after all these years.

[sweetdreams]

I was young. Probably around 5 years old. It was a pair of nylon stockings that caught my eye. I had to put them one. Played with them for about a day then mom found them and they disappeared. Too late. I was hooked.

[tiffyjo]

I was probably about 10 and stumbled upon some of my mom's old panties she had put in a rag bag in my closet in my upstairs bedroom. It was stuffed full of old washcloths, hand towels, pillowcases, etc. to use as rags. I reached in and felt them one time I was getting mom a rag and put it back in and grabbed a old hand towel. Feeling the panties caused a bit of an excitement, and feeling that nylon was super also. Later that night I reached in and noticed there were 8-10 pair of her panties neatly folded in the rag bag. Curiosity worked on me till that night and I knew I had to try them on. I took of my plain ole white underwear and slipped on her panties and i was so excited and looking back, I was hooked.

I would try them on whenever I had the chance to be alone and not be caught. Mom would have me help do laundry by taking her panties and bras into their bedroom and put them away. When I was home alone I would look around in my parents room and would find panties, bras, and pantyhose laying in a chair or over the ironing board. Her dresser seemed to have them in all the drawers and even found a couple of girdles. I would try them on about any time I would be home alone. I was worried she would be able to tell that they had been worn and even worried about the panties in the rag bag as they were the only items in it that were folded and stacked along the side.

Looking back the last few years at pictures of me when I was little, many of the pics look like the clothes I was wearing, they very likely may have been for a little girl. I have an idea that my mom may have very likely planned possibly on having a little girl and had many items of little girl clothing, but did it go a little further? Is it possible she put the panties in the rag bag for me to find? Did she leave her undies laying around and have me helping to possibly "encourage" me to explore those items. A couple years later I found one of her old, short nighties in the rag bag. Causing me to think that she actually knew I was trying her undies on and she was secretly helping me to do it. She never did catch me wearing her undies.

It's been about 50 years now and since I now am single, I have my own bra, panties and etc. and can enjoy wearing them almost all the time. Am I crazy to think that maybe she was maybe secretly encouraging me to try on her undies? If she were still alive, I would very likely ask her.

[Natalie5004]

3 older sisters that were a knock out.

[sometimes_miss]

I was molested by someone who told me that god made a mistake, and that I was really supposed to be a girl. He presented reasons why, and, as I was only a little kid, I didn't have the mental capability to challenge what he told me, so I believed him. After all, since I already believed in Santa Claus, the Easter bunny, and a god, what was one more weird thing to believe in? So he made me into his private little girlfriend, and that lasted until right before I started high school. By then, the damage was done; long term indoctrination can be very difficult to defeat, no matter how ridiculous it may be. So to this day, the concept that I was really supposed to be a girl remains in the back of my mind, no matter how much logic tells me that it's not true. So I always feel just a little uncomfortable when dressed as a male, and am only truly comfortable when dressed as a girl. I'm sort of stuck in a female mindset at about age 14, exactly around the time my abuser disappeared from my life. Forever waiting to become the girl I was supposed to be? (I didn't reach puberty until I was 17). I would continue to secretly try on my older sister's clothes whenever no one else was home. That was almost 50 years ago. So I was stuck, for life, with the desire to dress as a girl. Repressing the desire results in me becoming short tempered, irritable, having difficulty sleeping, and having a shortened attention span. Perhaps like a computer that bogs down when you ask it to do too many things at once, my mind simply cannot hold back the thoughts telling me that I'm a girl, so those thoughts come to the conscious level of my mind, and everything else gets pushed aside until I'm once again, able to push them into the subconscious.
Meantime, I sit here in my cheerleader's uniform, enjoying watching the game on TV, pretending I'm one of the pretty girls on the sidelines.

[RichardTO]

We had a female centric house when I was growing up. 3 older sisters, pretty domineering. I loved them and still do. I wanted to be one of them.

That was just like how I grew up. Sister, two stepsisters, dominant mother, and a stepfather who allowed the females to get away with what they wanted. Very female-centric.

[Jennifer2918]

I was in competitive roller skating and my mom purchased a pair of white tights for me to wear under my outfit. When she put me in them, them felt great. They did not work the way she intended, so that was that, but I remember the feeling. Then it was off to mom's panties and the rest is history.

[Michelle1955]

Started about 4 or 5 playing with the neighbors my age (all girls.
One day at a friends house she and i switched underwear and panties.

[Rosemaryjane]

Mom had pink strapless bra probably from teen years Used rolled up newspaper for volume She had a brown sparkly dress with a side zipper Remember them? It progressed to girdle and big girl bra more later

[Laura R]

I think I was about 10 or 11 when I first dressed. It was definitely my middle school years and this would have been in the late 80s.Wasn't something that I'd ever even considered prior to it happening but it clearly flicked a switch inside me and parts of it remain crystal clear to this day.

I was a member of the scouts and there was a fundraising event involving various troops from the county (this is in the UK). There was going to be all sorts going on throughout the day but on the evening there would be a big show with each troop contributing one or two performances. Anyway, some time prior my Mum asked what our troop was doing for the evening. I said how one of the leaders had written a play and we were going to perform that. Being an all male scout troop is was a predominantly male play but there were a couple of female roles. Mum started asking me what it was about and I forget how or why I even brought it up, but I clearly mentioned how no-one wanted to play the female parts, at which point she suggested why don't I do it? It had never crossed my mind to prior to her saying it and I wasn't too keen either, not to mention that I thought people would laugh at me. But she said something along the lines of how it would be fun, reassured me that it would be okay and that she'd help sorting the costume out. The role itself was of a mother in a family and I eventually agreed, although still wasn't thrilled about it. Fast forward and I get home from school one day and there was a bag full of clothes that Mum had collected from my two cousins, who were a few years older than me and who had sorted some things out that they thought would be suitable. She went through everything and picked an outfit, which just ended up being a knee-length dress, cardigan and some very low heeled shoes (photos exist!). I can still picture myself looking at myself in the mirror that first time I put the dress on and thinking I just looked silly. A couple of days later, I got back from school and Mum said something about wanting to have another look at me in the outfit. I didn't understand why at the time as she'd literally only seen me in it a few days ago. Turned out she'd been shopping and brought a bra (which she padded), some tights, a few accessories like a necklace and bracelet, had got a wig from somewhere, and wanted to see what I looked like with everything on. The thing I remember more than anything is her having to help me put on the tights and the feeling that very first time I wore them (they were a low denier tan/flesh coloured pair). There was at least one more outfit run through at home, as Mum wanted to try putting me in makeup, and by the time of the actual performance, I'd become much more comfortable with the clothes and the whole idea of it. Plus there had been a full dress rehearsal, so while I did get a few people laughing at me then, come the night a lot had people had already seen me dressed by that point. Also, as the photos show, when everything was put together, the clothes, the accessories, the wig, the makeup, I didn't look too bad!

Oh yeah, and the other female role, no-one else wanted to do it so one of my friend?s from the troops sister ended up playing it! So if I'd been a bit more reluctant or just said "No" they'd most likely have just gotten another girl to play the part I did.