How did it start for you?

[Chloe_S]

Did you always feel more femme than male or did you start experimenting with crossdressing and it progressed from there? Obviously it doesn’t fall neatly into those two categories, they’re just examples of what I’m asking. But what’s your story…?

[Lana Mae]

I was 5-6 when I wanted a dress! I did not get one! Sad! Then it was Panties only in my teens! Sporatically through 20-40's! I had no idea what all this was about! Maybe just naive or ??? At 65, my wife passed away! Next month, I was buying panties! Then I got on the net and ended up here! I have grown a lot in the last 3 years! I basically started just wanting to see my feminine side thus Lana Mae! Back at 5-6 the girl that caused me to want a dress was Lana! Mae was my mother's middle name! Short answer is yes it progressed from crossdressing to where I am now! Hugs Lana Mae

[cdinmd206]

I remember when I was in cub scouts we did a play and I was very disappointed when i did not get the female role. I would have gotten to wear a very frilly Mexican type skirt and blouse. It was about then i realized the sears and roebuck catalogs had the lingerie section and I spent lots of times looking and wondering what the items would feel like wearing them.
A couple of years later I was staying with my aunt for a couple of weeks during the summer. On a rainy day my female cousin and I were wondering what to do and my aunt suggested for us to play dress up. Well not only did I get to wear a frilly dress but I got to wear everything that females wear under their dresses. Long story short I spent the rest of my visit wearing my cousins things and loved it.

[xam]

I remember when I was in cub scouts we did a play and I was very disappointed when i did not get the female role. I would have gotten to wear a very frilly Mexican type skirt and blouse. It was about then i realized the sears and roebuck catalogs had the lingerie section and I spent lots of times looking and wondering what the items would feel like wearing them.
A couple of years later I was staying with my aunt for a couple of weeks during the summer. On a rainy day my female cousin and I were wondering what to do and my aunt suggested for us to play dress up. Well not only did I get to wear a frilly dress but I got to wear everything that females wear under their dresses. Long story short I spent the rest of my visit wearing my cousins things and loved it.

Interesting experience!

[Petra1]

I’ve always had an obsession with breasts and beautiful women. As I got into pre-adolescence, I started to wonder what it would be like to have breasts so I started experimenting with rolled up towels stuffed into one of mom’s bras under my regular clothes. It got to the point where I would stay home alone while the rest of the family was camping so I could have breasts all weekend. The rest of the garments started falling into place from there.

[Melissa_Me]

It started with satin under skirts when I was about 8 years old. It then moved to skirts, bras and blouses.
Suddenly I was fully dressed and enjoyed the variety of different outfits, styles and colours.
My normal attire was shorts and football shirts as out in public I was a lads lad but in my own secret mind I loved the feel and look of been a girl.
Things have moved on since and my amazing wife helps me improve and perfect my look and style, but I still have the lads lad look outside the house.
Xx

[Elizabeth G]

When I was about 10 or 11, since my parents ran a pretty tight shop and there wasn't anything else around the house to satisfy my adolescent curiosity, I started looking at the lingerie section of the Sears and J C Penney catalogs. After a while I realized I was becoming just as fascinated with what the models were wearing as I was with the models themselves. Things just grew from there.

[Angela Marie]

I began by wearing my mothers tights. I always wondered what it would be like to dress fully. I did not do it until I was about 50. But once I did I loved it.

[Robertacd]

Well I have always felt feminine, and I think in fourth grade I noticed girls in my class started wearing training bras I remember thinking "I should be wearing one of those"...

The rest is history, as they say.

[NancySue]

Growing up, I lived next door to two sisters and we would play together. I was around 8 or 9. One day, they were playing “dress up” and asked me if I’d like to join them. At first, I just watched...fascinated. They had some lingerie which drew my attention....especially nylon stockings, so I joined in. The instant I put on nylon stockings, I experienced very pleasurable feelings. That, to this day, started my cding progression. Hose, of all kinds are still my #1 favorite pieces of lingerie.

[Michelle1955]

Realized I wanted to be a girl at about 4 or 5. Switched underwear / panties with a gg friend at her house. Yes she was my age 4 or 5 also, the panties felt correct. Progressed from that point, nearly 60 years later.

[wendy]

I started when I was about 5, back then there was a thing called latch key kids, and I was one of them.

My mom would wash her panties and hang them up in the washroom to dry. I was fascinated, whenever I was in the washroom (door closed) I would feel the texture of the panties and there were so smooth, compared to the drab male underwear I was wondering.

One day after school, curiousity finally caught up to me and I decided to grab the pair of panties and try them on. It felt so amazing and so right. Since then, I have not looked back.

[Judy-Somthing]

Boy, seems like allot of us started at about 5. What I remember is my older sister dressed me up in her Ballerina outfit and after that I was hooked!
I wore that Ballerina outfit every chance I got until it didn't fit any more. I remember wearing the tights to school in 1st grade.
Maybe a physiologist can fix me, LOL!

[Tracy Irving]

Around the age of five for me as well. "Borrowed" a pair of my mothers nylon granny panties and never looked back.

[ronniegirl]

My earliest memory was also around the age of 4 or 5 when my mother dressed me in a pair of panties since all of my drab undies were in the laundry.. and the rest is history as they say...it wasn't till I was in my late 50's when I was divorced and found myself living alone that it has progressed to full blown dressing and outings . As an aside, somewhere in the back of my mind I remember reading something about our personalities are forever etched into who we will be by age 5 give or take a yr. That might explain why so many of us go that far back in our memories.

[Angie G]

for me I was 10 or 12 years old I would go in the attic where we rented. A lade renting there stored things up there being an only child I had alone time so I'd go up there and try her dresses, skirts and what ever I could find. My dressing went on and off till June 2006 when I got my wife to let me wear a skirt one very hot day . Now retired I dress about 95% of the time

[Barbara Black]

When I was three or four the girls of the neighborhood were playing dress-up. For whatever reason they dropped the dresses on the sidewalk and were playing across the street. I said to a friend, "Wouldn't it be fun to surprise them by dressing in their clothes?" And we did, partially. We were spotted before we had gotten dressed and dropped the dresses and ran away. Little did I know that to me it wasn't just 'fun' to tease the girls.

[Devi SM]

For me was around my 5 or 6 years old but I unconsciously had forgotten it may be erase from my memory because what I had in my mind was in my early 20s that, as a joke, I wear the whole day my of my wife's panties, a thong. I look my butt in the mirror and found it very sexy. Never again wear men's underwear.
Later being on therapy I start remembering those childhood hidden memories and later in teenage days trying ky sister panties and bras.....

[Cheryl T]

I too was 5 or 6 when I first had the inclination to try on my mom's clothing. First it was panties and I just loved the feel and look of the nylon styles she wore. Then I tried on a bra and the rest, as they say, was her-story.
It just felt so natural, even at that age, to wear these things. Later on I tried on a few of her girdles, and stockings and then heels and a dress. I never looked back from there. I just wish I had had the courage to tell her how I felt back then. I feel she would have been understanding and perhaps I would be in a totally different place today.

[Devi SM]

Cheryl, it's never late. I'm 60 in September. My transition began around 14 years ago but in HRT 13 months now.
This is the real me that people see now. No more hiding g...and I'm happy with a wife, 3 sons and one grandson...

[sometimes_miss]

Short version: Molested as a kid, told that god made a mistake and that I was supposed to be a girl, told that repeatedly over the next seven years and winding up believing it and trying to understand why. When you look for reasons for something, sometimes you start to see them even if they aren't really there. From then on, it become a self fulfilling concept, and, would pray and pray for god to fix me, all the time trying to learn how to be the best little girl that I could be. By the time I was in high school I had been believing it for many years, and only felt normal when dressed and trying to imagine what it was going to be like as a girl, and practiced behaving as one.
Seems growing up believing stuff like this just might affect a mind permanently, because even once I figured out none of it was true, the feelings never seem to go away.

Long version link is in my sig below.

[Rochal Tukque]

I started wearing my sisters bras and panties when I was about 7 by the time I was 9 my breasts had outgrown her little B cup bras. Today I have average C cup breasts and since Im now dressing for public outings I use silicone over lays to go up one full cup size. The point I would like to get comments on. The over lays add about a pound to each breast and the thing I notice is that when I’m wearing them it’s as if that’s what has been missing. Something that should’ve been there all my life and I’m not talking silicon and they are not overly large for my body type. Anyone else feel that way?
If someone would ever take me by the hand and clue this dummy in on how to post a picture on here from a iPad I would get my picture up.

[Georgina]

When I was about six I became aware of girls wearing petticoats. For some reason my first reaction was I want to wear those. I never wanted to be a girl and always thought it was unfair that boys couldn't wear the same clothes as girls. I did wear petticoats and everything else and still do 60 years later.

[GretchenM]

Wow! What fascinating responses to an important question. Pretty much the same story for me. First feelings at 4 or 5, experimenting at 7 and 8, told my mother I wanted to be a girl. Got denied (it was 1953). Went into denial and suppression for almost 60 years with a secret second side of me I went to when seriously dysphoric. In 2012 decided I could no longer fight her and came out. Hellish at first, but then settled into a comfortable pattern with an agreeable DADT pattern between my wife of 50 years and me. She allows but does not want to see me fully dressed, which I rarely do anyway. But my bits and pieces approach is acceptable so long as it is not strongly evident.

The pattern that all the folks here have expressed is exactly what the psychologist have found to be true of nearly all CD/TG people. Late bloomers are rather rare. That evidence for this being some kind of predisposition that once triggered, usually as children, can never be turned off completely. Pretty typical predisposition pattern. No mental illness or perversion - it is just the way some people are constructed. You are all so wonderful.

[Maid_Marion]

Ironically, my wife started it! She knew I was transgender but brought up the idea of wearing female clothes to put together an age appropriate wardrobe for work, as I was still wearing the same outfit for twenty years. I'm am XS petite hourglass, which means you can't find men's clothes! Anxiety issues. Age in which it can be hard to get another job. Not only did I get lots of female tops inexpensively via Ebay but also VS PJs! She had body issues and wouldn't go near VS. She brought up underdressing with panties but I didn't go there while she was still around. A few years later I realized that retail therapy would really be helpful. Especially since I had lots of closet space to fill. :o

[Cheryl T]

wish that it were that easy.
You are so lucky to have an understanding wife that has stayed with you. My situation is different. We have talked and talked and I know that would not be the case with us.
I'm not willing to put her in that position, I love her too much.

[Connie D50]

I remember when I was in cub scouts we did a play and I was very disappointed when i did not get the female role. I would have gotten to wear a very frilly Mexican type skirt and blouse. It was about then i realized the sears and roebuck catalogs had the lingerie section and I spent lots of times looking and wondering what the items would feel like wearing them.
A couple of years later I was staying with my aunt for a couple of weeks during the summer. On a rainy day my female cousin and I were wondering what to do and my aunt suggested for us to play dress up. Well not only did I get to wear a frilly dress but I got to wear everything that females wear under their dresses. Long story short I spent the rest of my visit wearing my cousins things and loved it.

I was the female role lol and then dress as a girl for the cub scouts Halloween party

[Stephanie47]

My mother would do the laundry in a washing machine kept in the kitchen. It was against the rules of the housing project to have a washer in an apartment. She hung the laundry to dry on a clothes line running down the length of the hallway to the bedrooms. There was also a drying rack hung over the bathtub. I was attracted to her nylon slips. I loved the feel of the material. I would caress or fondle the material as I passed by. I progressed to taking them off the clothesline and trying them on. There was no desire to be a girl. I just was attracted to the feel of the fabric. She also hung her floor length nylon nightgowns which I also loved.

When I was in kindergarten my teacher complimented my cowboy shirt one day. She referred to it as a "blouse." I let her know in no uncertain terms that was "a shirt and not a blouse!!!" This awakening did not occur until my mother started doing the laundry in the apartment.

Why? Now becomes the difficult part of trying to figure all this out. I was a post WW2 baby. Our family had lived with my paternal grandmother until we were able to move into a post WW2 apartment building for veterans. I was three years old. I remember I was still in a crib. Some years later I started having visions of myself as a young dead woman laying in an overgrown lot. I was dressed only in a white slip. I still have that imprinted memory. I always found it unusual because we did not have a television set. So, there was no news to watch. I could not read yet. I did not go to school yet. This was something I would not have encountered. Why would a four or five year old have an image like that? Several years ago my wife started watching a program series of kids with past life experiences. I did some internet research on the subject. Most of the research indicates the child usually forgot those experiences as he or she got older. Of course, all this hinges on whether one accepts that premise at all. My wife does believe it is possible. If she and I were to ever have a sit down and discuss my cross dressing I would bring it up. I always found it funny that my love of women's clothing started with my mother's white nylon slips and that image of myself as a dead young woman in a white slip laying in an overgrown field.

[Palaina Nocturnus]

I would mess with my mothers clothes when I was around 4 or 5. There was not one hint if sexuality to it for me. I did this until I turned 12. Once I discovered sex and females, I started to play with the clothes of whomever I was dating.

It wasn't until I was about 24 that I met someone that helped bring out the CD in me and I was able to finally engage in my sexual fetish. Since then I was with 3 people and only did a little around them. My current relationship I decided I was gonna be me 100%. Today I'm 42 years old and have been CDing since around 2000

I do not have facial or body hair at all anymore, compared to most of my life being forced to keep a goatee. I got rid of all my baggy clothes and most of my Male dominated clothes in exchange for skin tight clothes purchased solely in the women's section. I even buy my sandals and shoes from the womens section lol

[Brandie.n]

When i was 14 my mom suggested i use her Elvira costume for halloween slinky dress,heels and pantyhose with fishnets over.I was hooked

[Rochal Tukque]

My mother would do the laundry in a washing machine kept in the kitchen. It was against the rules of the housing project to have a washer in an apartment. She hung the laundry to dry on a clothes line running down the length of the hallway to the bedrooms. There was also a drying rack hung over the bathtub. I was attracted to her nylon slips. I loved the feel of the material. I would caress or fondle the material as I passed by. I progressed to taking them off the clothesline and trying them on. There was no desire to be a girl. I just was attracted to the feel of the fabric. She also hung her floor length nylon nightgowns which I also loved.

When I was in kindergarten my teacher complimented my cowboy shirt one day. She referred to it as a "blouse." I let her know in no uncertain terms that was "a shirt and not a blouse!!!" This awakening did not occur until my mother started doing the laundry in the apartment.

Why? Now becomes the difficult part of trying to figure all this out. I was a post WW2 baby. Our family had lived with my paternal grandmother until we were able to move into a post WW2 apartment building for veterans. I was three years old. I remember I was still in a crib. Some years later I started having visions of myself as a young dead woman laying in an overgrown lot. I was dressed only in a white slip. I still have that imprinted memory. I always found it unusual because we did not have a television set. So, there was no news to watch. I could not read yet. I did not go to school yet. This was something I would not have encountered. Why would a four or five year old have an image like that? Several years ago my wife started watching a program series of kids with past life experiences. I did some internet research on the subject. Most of the research indicates the child usually forgot those experiences as he or she got older. Of course, all this hinges on whether one accepts that premise at all. My wife does believe it is possible. If she and I were to ever have a sit down and discuss my cross dressing I would bring it up. I always found it funny that my love of women's clothing started with my mother's white nylon slips and that image of myself as a dead young woman in a white slip laying in an overgrown field.

Very interesting! In later years I did a past life regression. I was a 11 year old girl that died in a house fire set by her brother. The details of the regression were verified to that date and the place. Which made sense to me as I felt as a kid I was finishing something of some sort. It explained a great many things. Including a birth defect that left me some feminine attributes.

[Fiona Lindum]

Started at about 13 when I wore a pair of tights. I was about 30 when I started wearing dresses and skirts.

[BTWimRobin]

When I was around 4 or 5 I used to get into my aunts' closets and play dress-up. Then around 11 or so I discovered my mom's nylons hanging in the bathroom. Once I tried them on, I was hooked. I my late teens, I had a girlfriend who used to dress me up. The desire to dress subsided and in my 50s it came back and I have been enjoying every minute of it.

[Bruce64]

I started as a Teenager, start buying Panties in my mid twenties and here I am now wearing Brassiere to work.

[Pumped]

I also started young, I really don't remember my age but I would guess 3- 5 years, and I don't remember for sure what set it off, but I remember a TV show with "show girl" dancers. You know the shiney tights, high heels, beautiful long legs, sparkling leotards, plus these girls had tail feathers! I rember snitching one of mom's bras and stuffing it, wearing a t-shirt and undies and trying to memic the huge fluffy tail the dancers were wearing. I also remember the feeling I got. Being so young I didn't understand it, but now I realize it was a sexual feeling. Even at that early age my body knew what was going on even though my head didn't! Dressing for me has mosly been sexual fetish first and just wanting to be feminine has been second.

[ChubbyLeahCD]

Did you always feel more femme than male or did you start experimenting with crossdressing and it progressed from there? Obviously it doesn’t fall neatly into those two categories, they’re just examples of what I’m asking. But what’s your story…?

I remember at age 4 or 5, being a pre school and waiting on my mom being the last kid there. The owner of the place was talking to another mom and I stood there and saw her in a skirt, tank top and t-strap sandals stand with one hand on her hip, feet apart, one in front of the other and then mimicking her stance.
Around the same time I would go to my grandma’s and she would have her panties in the shower as she would wash them for whatever reason. I’d always try them on. Then around 12 or so I took the plunge and would dress in my mom’s clothes while i was alone at home.

[KimberlyCasino]

I had an aunt that used to live with us when I was a kid, maybe 10 years old. When she wasn’t home I used to sneak into her room and go through her panty drawer. It was a big turn on to examine them but one day i decided to put a pair on, I knew i liked it right then and there but didn’t really continue with it. She moved out and I wasnt able to go through her panties any more. Flash forward to a few years ago when i was like 25 and my ex girlfriend used to leave panties and stuff at my house and I started trying them on again lol. It made me so hard but then she caught me because she could tell they were stretched out a bit lol. I had to stop but she ended up breaking up with me anyway lol. Then a few weeks ago I was talking to a trans woman I met online. We were chatting and she intrigued me to try it again and for real this time. I went to macys and bought a pair of red lace panties and black nylons and dressed up. I loved it so much I went on a victorias secret shopping spree and bought all kinds of nylons and even a pair of stiletto heels on amazon lol. I have been completely entrenched in it for the past few weeks and i love it. I feel so alive and My sex drive has never been higher. I really wish I could find a woman or trans woman to dress with in real life. It gives me such a rush.

[SaraLin]

I can't say for sure when it really started, since I've always felt like I was supposed to be a girl - and tried to dress the part whenever I could.

One of my earliest memories (apologies to those who have seen this before) is staying overnight at my grandparents' house. Since they didn't have PJ's for me, my grandmother would break out a housedress of hers, put a belt on me, and hike the skirt up to where I wouldn't trip on it. I WAS IN HEAVEN! I remember announcing that I was now a girl. Of course they ignored my "childish nonsense" (I think I was about four at the time). Needless to say, I found every excuse I could to sleep over.
Years later, I liberated some outfits from their attic. I think they must have been dresses, etc. that my mother and/or aunts when they were younger.

Of course, I also "borrowed" a few things from my sister - until I got caught with them in my possession, and got in trouble for it.

[rhonda]

I was about 12 for some unknown reason I tried on a dress and from there it started and hasn't stopped since

[Diedre]

Around 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 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.

[Victoria_R]

For me I have two instances. First one was when I was 6 my dad was dating my step mom and he dropped off at her place to play with my younger step sister while he went to work. They had a small pool in the back yard and my step sister wanted to go swimming. I couldn't go swimming with her because I didn't have a bathing suit. So my step mom didn't want me to miss out on the fun gave me one of her bikini bottoms to put on and go swimming. At first I was scared because I was wearing a bikini but I got over that quickly because we was in the back yard and nobody could see. The feeling of the wet bikini felt good to my body. I saw my step mom laying out sun bathing in her bikini while we was swimming and I felt like I was her daughter. After that day I loved bikinis. The second time was a few days later my dad dropped me off again to play with my step sister and he had to work late so I ended up having to spend the night there. Well playing all day I got dirty and had to take a shower before bed and I didn't have any extra clothes so she gave me one of her t shirts and a pair of black satin panties and sweatpants to sleep in. When I pulled the panties up my friend down there got all happy and I didn't understand why but I felt like I was in heaven. It felt so good I wanted to wear them everyday. The next day I asked if I could keep them and she laughed and said no that's women's underwear and that was the only time I was going to wear them because I didn't have extra clothes. Well from that day I wanted her panties again and a few months later my dad married her and at night when they was watching TV and I was supposed to be in bed I was like a Ninja trying to find them black satin panties again so I could sleep in them. When I found them I was so happy and was hooked on panties. Then years later when she was not home I would try on her dresses and other stuff. From then on I been dressing ever since. But she did find out I did take her panties lol.

[ShirleyN]

I was 13 when I started dressing. It was just out of a mild curiosity when I got into a beautiful floral patterned dress. I just loved the feeling of it. Felt so relaxed and it's been ongoing every so often ever since.

[Lea]

Over the years I learned from my mom, and my father when he was dying that they wanted a girl. They already had a boy so the second child, me, was supposed to be a girl.
Before I was old enough to go to school mom dressed me as a girl. She would tell me that people thought I was a pretty girl. When it was time for me to go to school my hair was cut, clothes changed and off I went.
I did not have the closeness with my mom after that point as when I was treated as a girl. When my dad was dying I took a picture of my daughter into his hospital room. I asked him if he recognized the picture and he insisted it was me dressed as a girl. He told me my mom used to dress me as a girl.
Mom has admitted she wanted a girl, and that people used to think I was a girl but has not admitted to dressing me up.
When my mom went to work I used to wear her clothing as much as I could.
So I do not remember a time when I have not dressed.

[CynthiaD]

My first memory is begging my mother to wear nail polish when I was three. She complied, and I ran outside to show all the other kids in the neighborhood. They made fun of me because “only girls wear nail polish,” but I didn’t care. I also remember asking my mother to tie ribbons in my hair from time to time. She did, but they kept falling out because my hair was too short. By the time I got to high-school, wearing female clothing, borrowed from my mother, was just something I did. By that time I was dressing fully, with socks stuffed into my bra. Great days.

[susan2010]

I remember wearing my sister's full white petticoat when I was about 4. I don't think that was the first time I had it on. After that it was mom's slips and nightgowns.

- - - Updated - - -

That sounds a lot like me. I was just a bit younger, but petticoats got me hooked (and still do!)

[donninacd]

Tried on my mothers pantyhose a couple of times as a teen. Didn't do anything further with it for 3 decades.

[Kelly63]

Definitely pantyhose for me! Still my favourite and don’t feel dressed without them.

[RobynB]

I did not have a sister, but I purchased my first petticoat in the 60's from Sears.

[StephanieIndy]

I had always felt more femme from as early as I can remember. I remember wearing my sisters clothes from an early age (and being told off by my parents because boys don’t wear girls clothes). I didn’t understand everything then, now I’m aware that I’m trans and everything makes sense, but growing up was tough!

[Bruce64]

I have a mental obsession with Panties, I love the shspea, colors, feel,fitting, so I started going to stores and buy secretly when I was in my mid twenties, now I wear bras, slips, pantyhose, it's a neverending obsession.

[Karmen]

I don't know why, but as far back I can remember, I was always drawn to female clothes and shoes. I never felt as a woman hidden in a male body, but always wanted to wear female clothes. Need for makeup and wigs came much later, when I wanted to go outside and wanted to look as closely as possible as a woman.

[Bea_]

I have vague memories of my older sister and a friend dressing me as a girl once when i was maybe 4 years old. I'm not thinking that had any major impact though. Not a trigger for me.

As an adolescent, my mom and the same older sister would leave bras hanging in the bathroom. When the testosterone kicked in at age 11 or 12, I'd put one on just to have something feminine to am the hormones at. I never really associated the bras with my identity. Still not a trigger.

I grew up in tighty-whitey's and when I began buying my own underwear, I'd always look for men's bikinis. I'd always check the underwear section when I went to any department or clothing store to see if there were something 'different'. There never was.

About ten years ago, I tried on a couple of pairs of my wife's cuter panties and decided that THAT's what I'd been looking for in the men's underwear department. Shortly after that I bought 2 or 3 pairs of panties from a dollar store, not knowing what size to get and buying a couple of sizes too small.

Shortly after that I 'confessed' to my wife that i'd like to wear panties and we ended up at Kohl's one afternoon. She had me wander the store while she chose some items that she thought she could handle. She chose well. We left the store with probably a dozen pairs of panties, mostly bikinis, but also some really nice thongs. Within the next year or so I hit the first hundred pair.

I expressed interest in leggings and got 'approved'. Then some tops. She shocked me by holding up a dress that she thought I might like on one trip out. I don't think I'd ever mentioned that I'd like one before that. On another trip she picked out a really cute sundress.

I retired last year and spend most days that we don't have a big agenda, at home in something femme. No forms. No makeup. Full beard. But, me in a dress, or skirt and top, or leggings or...

[chrissietoo]

Fascinating and sexy thread! I don't know what I was doing at age 5, but I do remember I was very interested in girls and their clothes. Out of the blue I asked my mom if I could be a girl for Halloween, and she put together a costume for me...I was in bliss! I remember also the girls as they first were wearing bras, and the nice fuzz on their legs, which then disappeared. I noticed everything--soft sweaters, crisp blouses, silky hair, and did I mention bras?

I was just growing a couple of pubic hairs when I would spy on an older girl in an apartment across from ours, because once I saw her in her bra. One morning I saw her hanging a bra on the line down at the laundry, and I was compelled to take it. I put it on a couple of times, but it didn't fit at all, but I kept it as a prize possession. Puberty is a big blur, and then at 16 my girlfriend left her bikini in my car, and I was seized with the compulsion to bring it to my room. When I put it on late that night, a jolt of electricity shot through me, as well as a huge sexual rush. If I wasn't gently hooked before, I was that night!

[laura.lapinski]

Chrissietoo Mine started with a bathing suit too. A one piece. I felt the same as you stated when I put it on an looked in the mirror. I liked the way it felt on my body, hugging and snug. I was about 13, but I had some thoughts in years before that.

[Manasi]

When I was about 10, I envied girls at school, they got to wear dresses, have long hair, and wear jewelry and later makeup. I started trying on my mum’s clothes when I was at home alone. I started buying my own clothes when I moved to the US to study, and only started coming out to friends about 3-4 years ago.

xoxo,

— Manasi

[Dana3]

Ever since I can remember as a young boy 👦 I've ALWAYS have been drawn to, towards, enthralled, fascinated with girls, women, femininity, and all things associated with same.

When I was younger, prior to going to school 🎓 around 3ish to 4 or so? My oldest Sister would play with a neighborhood 🙋 girlfriend.

They wouldn't let me join in only if I dressed as a girl also. Since what they were playing was for girls 👯 only.

About this time, we had a 16-year-old girl 💁 cousin. Puberty being what it was, I suppose, she would molest me, until once she hurt 🤕 me and I threatened to tell my Moma. 😟

I had no awareness of the differences between 👶 boys and girls 👩 other than the obvious
external ones. At my age, I never able to connect the dots.

Later I would enjoy looking at and through the various catalogs, Sears & Roebucks, JC Penny, Rommans, Lane Bryant.

Later I became fascinated with lingerie, and Fredricks of Hollywood ads that I would come across in various magazines.

My parents 👨*👩*👧 separated and divorced. My two ✌️ sisters went to live with my Mother in another state, I stayed behind and lived my Grandparents on my Dad's side of the the family.

Along about the time I was in the seventh grade, my then 16 year old sister came to stay with my Dad and I.

I distinctly remember "To understand girls, be a girl!". And I tried on a pair of my sisters underpants.

,🤤 😲 🙂 🙃 😍 😘 😍

Things progressed as they say from there.

[Cassie38]

I remember first trying on my mom's pantyhose/nylons when I was around 5 or so. Do not remember trying on anything else fem after that. When I was about 21-22ish, my gf at the time decided to dress me up for one of her friend's Halloween party since I had long, natural wavy hair at the time. She helped me shaved my legs at the time and picked out a few outfits at a thrift store. I was hesitant at first at the idea, but a rush fell over me when I first tried the items on and she did my makeup to make me look fully passable. The rush intensified when I caught a few guys checking me out at that party. For full disclosure, her friend who hosted the party was gay and there were a lot of gay guys there. I dressed up quite a few times for my then-gf.

[susan54]

When I was eleven a girl I was completely infatuated with was sent away to boarding school. The school was just for girls. I imagined dressing as a girl so I could be with her. It was her who made me excited, not the thought of being dressed as a girl. I have no idea if that was what set me off. My mother was always very fastidious about what she wore and made comments about what women on television were wearing and I suppose deep down I am seeking her approval when I dress up as I like to put a really good outfit together even with the right accessories. To this day what I like to achieve is an outfit that looks good not that makes me feel like a woman - I don't - I feel like a man no matter what I wear and identify only as a man. So I only speculate about why I do this. As a grown-up I formed a relationship with a woman who had gone to the same school as the 11-year old I worshipped (pure coincidence). I am not sure if it is a hobby or an obsession and it is possibly significant that my younger sister is as obsessed with women's clothes as I am and we both have far more than any normal person would.

[JennaDcd]

Not sure how old I was, maybe 6 or 7, but I remember seeing my mom's silk panties in the clothes basket and getting aroused. From that point on I was hooked. Whether it was my mom's, my sister's, or an aunt's when we'd visit, I spent my youth sneaking off with their silk or satin panties and trying them on. Never got caught, thankfully! Occasionally I'd also sneak off with their bras, stockings and any other lingerie I was in the mood to try on. Now, in my early 40s, I have completely accepted that it's who I am and will likely never go away.

One thing I have realized though, is that for me, it's purely sexual at this point. I only dress when I'm aroused ... or dress to get aroused. Never just to relax or because I feel like a female trapped in a man's body.

[Lacey New]

I started in my early teens. Back then the girls in junior high school wore skirts and would occasionally provide an intended glimpse of panties. I was also fascinated by seeing bra straps on budding breasts. So I would look at the panties and the bras and would imagine the wonderful things underneath them. Well, Mom and a sister a year younger provided plenty of lingerie in the hamper and one day just out of curiosity I decided to see what it felt like. The fabric of the panties was soft and silky and exciting. I had a few moments so I put on a pair and you can imagine what happened. Well, not only was it exciting but it was addicting. If panties were great, panties and a bra were even better. Then stockings, slips and any other lingerie I could find. Pretty much the rest is history.

[Ericka_d]

I was around 10 when some one was watching the weather channel, and I noticed the suits the ladys were wearing. For some reason I wished I could wear them. Now at 35 years old. Im pretty sure that is why I love female office attire, and it looks good on me. Compared to normal clothing. Like jeans, and a top. While I pretty munch wear womans clothing every day. I really wish I could wear office attire all day every day.

[dana digs sweaters]

Did you always feel more femme than male or did you start experimenting with crossdressing and it progressed from there? Obviously it doesn’t fall neatly into those two categories, they’re just examples of what I’m asking. But what’s your story…?

Being the only boy with 5 sisters (3 older) , there was no how, no way that I wasn't going to end up wearing their clothes.
Seeing Flip Wilson and Klinger from M*A*S*H* on a weekly basis dressed as a woman gave them plenty of ideas.
Could also include Bugs Bunny, the 3 Stooges and Milton Berle reruns :D
A lot of skits were done where I was in their clothes. Of course I never refused :)
How could I when it was fun to me? Always funny to them also.
Of course I experimented without them from age 7 on.

305628

[candice.aihara]

Long ago, I slipped into my first pair of panties. They were purple with tiny white stars. The panties were a bikini cut made of soft cotton with a tiny lace trim along the waist. I felt excited and nervous as if I was doing something deliciously forbidden. My head was spinning. Around the same time, I paired the panties with a demi bra. It was lightly lined for a subtle lift and had underwire cups. It was probably made of nylon and spandex. I distinctly recall it was coconut white. The feeling was sublime!

At some point during a hot summer evening of my (very) early teen life, when my parents were away, I did something really bold. I wore a complete feminine outfit while bike riding around in my neighbourhood. I had on a cap, bra, panties, denim short shorts, a thin t-shirt, and a flannel button up shirt tied about my waist. On my feet were sneakers. I walked into a convenience store and I purchased candy or a magazine; I forgot which exactly. But I do recall my heart was thundering the whole time!!

[HelpMe,Rhonda]

One of my earliest memories is putting on a pair of Mom's earrings, and some sort of big reaction happening.

Later on it was putting on a dress she had for some big event, when I was somehow old enough to be home alone, and then it kept going and going and going.

[GeorgeA]

Re: post#10 NancySue.

Nylons started my cross-dressing and are an essential part of my daily attire. Without nylons I'm not dressed.

- - - Updated - - -

Starting age.

Most posters said they were about 5 when they developed an interest in lingerie, etc. I think age of 5 is the transition point from being babies to pre-schoolers. Our curiosity develops and we start exploring the world around us. We start being independent and that includes varieties of clothing. I also was 5 when I tried to put nylons on. I wrote about it in my introductory message when I joined here.