The early years

[Debbie Denier]

After trying my mothers tights/ pantyhose as a youngster, little did I know it would change my life forever. I started to dress up in her tights and black slip every Saturday morning when she went shopping.I would prance in front of the mirror until the happy ending would be followed by guilt, disgust , shame and a quick change back to drab. . I was fascinated by my French teacher at school. She always dressed in pretty dresses, tops , skirts and nylons. Unlike the teenage girls that wore uniform and white socks. I was attracted to her but also wanted to look and be like her. This confused me. I knew I wasnt gay but why did I feel and have these desires?. . Did any body else have these feelings and desires when a teenager growing up?

[Genifer Teal]

I had a short teacher who always wore very high heels. That created a curiosity how she could walk in them.

[kimdl93]

I had such fascinations very early in life despite growing up in a farm family of mostly males. the women in my world wore simple, utilitarian everyday dresses and seldom any makeup. I did my best to blend in as a typical farm boy, but the affinity for feminine things proved to be deep and unshakable.

[Fiona_44]

I had a 4th grade teacher who always dressed nicely, mostly in nice dresses. I always admired the way she looked and that may have helped jump start my interest in women's clothing.

[Lilly Diadem]

Teachers in the 70's & 80's wearing tan or similar hose/stockings with wedge or heeled sandals did it for me; if you caught a glimpse of painted toe nails too that added to the pleasure especially if worn with a pretty Aprinted dress or skirt blouse/knitwear combo.

I was intrigued by them but also wanted to dress like them which was very confusing - still do and still is:)

[Geena75]

It was in the late 60's and early 70's I tried on pantyhose and then a dress. This was the time of short hem lines and brown nylons and I was fascinated by the young women I saw. When I dressed up in my limited way it was so exciting, but guilt was also waiting for me when it was over. Hiding things and eventually purging naturally followed. Is it any wonder that it took over 40 years and finding support from sites like this that I ever tried anything more?

[alwayshave]

Debbie, I often wore my mother's clothes. However, as I had nuns as teachers, there was no wanting to wear what they wore or any sexual attraction.

[Lacey New]

I started back in the mid sixties with my mothers and sisters nylon briefs. Back then, girls wore skirts or jumpers to school and watching them get in or out of school desks sometimes rewarded me with a show. Obviously I liked what I saw. And even the teachers wore skirts. We had one teacher who would sit on her desk and lecture. All the boys sat in the front and paid close attention.

[Lorna]

I couldn't help identifying with the sentiments expressed by Debbie Denier even though I suspect Debbie is younger than I am. That's because she was trying her mother's tights...tights didn't appear as standard female hosiery in the UK (where Debbie and I live) until the late 1960s. So my mother wore nylon stockings held up with open girdles. But, yes, like Debbie, I tried those and, also like her, tried mother's slips (they were white, not black).
In my part of the UK at the time, schools were for boys or girls, not both, so almost all the teachers at my secondary school were men...so no attractive female teachers to observe. Instead, it was girls going to and from nearby girls' schools that began to attract my attention in my teen years. Some of those girls started to wear stockings, instead of socks and that intrigued me: did they wear girdles like my mother's to hold up their stockings?
Cutting a long story (post) shorter, I began my lifelong quest both to learn about what girls - later, women - wore and to try to experience it for myself. Once I discovered girlfriends, I began to use every possible opportunity to learn about their clothes, what they liked and disliked wearing and why. I largely lost interest in my mother's things and concentrated on enjoying being with and learning about young women around my own age.
I learned such a lot. Not least was the realisation both of the huge variety of clothing available to girls and about how they made their choices. Learning (slowly) about underwear was a special interest: I hadn't thought much about bras (didn't try my mother's) but realised that girls "needed" them and were sensitive about them. (I suppose that's why naughty boys would sometimes try to snap girls' bra elastic!) The discovery that one of my girlfriends always wore suspender belts while another wore elastic roll-ons and one of her friends (a rather well-built girl) wore what felt like armour plating (apparently a boned girdle and long-line bra) set me off wondering what such contraptions would be like to wear.
Other female attractions preoccupied me for a good few years after that but, eventually, opportunities came along to satisfy my curiosity....and then, through the miracle of the internet and sites like this one, realisation that many othhers shared similar interests.

[Connie D50]

When I was young all I needed was a sear's catalog, would start in the lingerie section then pick a nice dress to wear in the dress section and finish in the heel section.. :)

[Maria 60]

Oh my goodness all the flash backs, especially that Sears catalog. But then again back then if you seen a bra strap we were in la la land. Debbie it's funny you mentioned French teacher because we had a French teacher who was short and wore high heels and short skirts and always wore pantyhose. I will never forget when I was going down the stairs and she called me. I looked up and between the iron railings I got a beautiful view of her very colourful panties and the gossit of her pantyhose. That image was imbedded in me for years and thanks to you it's back.
Unfortunately this thread does remind me of the dreaded guilt. It was so unfortunate so much joy and pleasure had to end always ripping everything off like the women's clothes were burning my skin.
Even after I told my wife afterwards I would apologize to her for being this way, and she was the one telling me to stop trying to figure it out and feeling quilt and just enjoy this gift I was given. She always sees things in the positive and I believe she was the best therapy.
Well thanks for the flash backs, now I have to go see if I have a pair of colourful panties like that French teacher had on.

[EmilyShy]

I not sure what compelled me to try on my mums stuff,( lingerie mainly) but i was just drawn to it and have been since. It wasn't until later I progressed to dresses, then make up etc. Looking back now she must have known but has never said anything.

I did in the late 70's have a teacher at primary school that fascinated me as she always wore very high heels and make up (not very pretty though) but I could not stop looking at her heels. We must of had a no heel policy in the assembly hall as she always took her shoes off whilst in there at which point she always walked on tip toes as if she was still wearing her shoes lmao. She also drove a Triumph TR7 which was comical as well. Looking back at it now it still makes me laugh.

Emily xx

[Lacey New]

Oh the Sears catalog was wonderful with the color pictures of the pretty women wearing bras, slips and full cut nylon briefs. It was this young teenagers Playboy at the time

[ColleenA]

In my case, it wasn't my mother's clothes too much, though I of course tried on some of them. Instead, it was an older sister's. She was pretty and popular, and it seemed she had it all, including a wardrobe of very attractive clothes. When I was 10, 11, 12, she was in high school, and I so wanted to be just like her. (Meanwhile, my male urges caused me to pant after the many hot friends she had when they would stop by the house.) When I was about 14 or 15, there were even times when I somehow had the house to myself overnight, so I would put on one of her nightgowns (I remember a flowy, royal blue one fondly) and spend an hour or two laying in her waterbed.
I have many happy memories of my time going through her closet and dresser.
Did I have the feelings of guilt and shame that others have mentioned here? Certainly. But they don't live on so much in my remembrance.

[Stephanie47]

Oh, how I remember the new English teacher at my all boys high school. Miss Kelly had long blond hair. She was drop dead gorgeous. She wore tight mini skirts and sat on the edge of her desk. She knew what she was doing and enjoying it. She had the undivided attention of all those teenage boys.

Me? The only clothes I had access to was my mother's, primarily under garments and a nightgown. There was one sun dress I was able to wear. I also had shame for what I did after I shed the clothes. I was full of self-loathing. It was confusing to lust after pretty girls and movie starlets who were unobtainable and hear that males who wore women's clothing were homosexuals. My parents were homophobic and tried to catch me in the act. They came close.

[DianeT]

I think being attracted by a woman and wanting to be like her at the same time is the very essence of being a crossdresser for many of us. I am still trying to crack that mystery. The fact that it seems so obvious to me and at the same time out of my reach to explain is what puzzles me to no end. The best interpretation I have come to is that I want to capture her mojo and experience the sensation of being her. Of course that supposed sensation is a construct of my own feelings and sexuality when I look at her so the mojo I am trying to steal is very much in my imagination only.
I see that a lot of us felt guilt after a session. I never felt any guilt. Fear to be caught, yes, but never any guilt, whether I engaged in a sexual activity or not (I crossdressed a long time as a teen without any sexual activity, but that doesn't mean the thing wasn't sexual. It was the driver definitely).

[il.dso]

Most of us were crossdressing way before the internet.
Feelings of isolation, confusion and phenomenal pleasure were ever present, but I always thought I was the only crossdresser in the world.
The internet and this website have clearly proven that's not the case!

[KrissyTN]

I started trying on bras, then later on panties from the age of about 7. Not really too sure what I was doing back then, but our clothes hamper was in our bathroom and my Mom would sometimes fold her bra and leave it on top of towels in the bathroom closet. Things picked up speed as I entered middle school as my siblings were either older or younger than me, which meant they were not in the house for about an hour every day. Having gained lots of information/ideas from Sears and Penny's catalog's at our house or my grandparents home, I used that hour wisely to search for anything I could dress in from my Mom's clothes and even some of my sister's clothes.

One afternoon I had some time at my Grandparent's house by myself and I discovered the Playtex "all in one" 18 hour girdles with the garters that my G'ma wore....that helped continue my journey and my search and from this time in my life forward I have always taken notice of women's fashion, especially if it involves heels, hose or nylons.

[Meg]

I think we all had similar paths. I was always very envious of what my sisters and mother were wearing. It all seemed so much softer and sensuous than male drab. And who could not be curious by just reading descriptions in the Sears/JC Penny catalogs. They described just how nice each garment was to wear. I was much bigger than my mother and sister after about the age of 13, but was able to buy pantyhose on my own and some lingerie. I would love to have bought skirts and dresses too, but did not have that kind of money. Yes, I started buying fem in person at a young age and never looked back. Hugs, Meg

[Erin Lafleur]

Lacey, I know exactly what you mean. The Sears Catalog, (along with Mom's slips, stockings and panties) were my gateway drug to this fabulous world!
I'm sure that's why I have a particular attraction to period women's wear...
I just saw this come up in my FB feed today and thought I should post a fond memory. It does make me somewhat nostalgic.
Oh, it certainly got the job done alright, but likely not in the way that this chap intended!

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[SophiaRose]

Amazing how much we have in common. That darn Sears catalog!

[Monique65]

It was the JC Pennys catalog for me. There was a Pennys store in town and every time my mother took me there, I would secretly peek at the lingerie section. Occasionally she would need something from it, and I was in heaven following her with wide eyes, seeing those things up close. I suppose she noticed my fascination but never said anything.

[KrissyTN]

This thread also brought up a memory of many Saturdays while visiting my grandparents, Mom, G'ma, me and my sisters would go out shopping. Usually it was the mall, which had a Frederick's of Hollywood (LOVED walking by there!) amongst other stores. Sometimes, we would go to the "downtown" stores - which usually meant dress or gown shopping. I remember seeing many of the dresses, and lots of lovely - Vanna White style - gowns during those shopping trips. My mom would always tell me to bring a book along so I wouldn't be bored. I wasn't bored! LOL!

[racquelr]

I don't recall we ever got the Sears catalog, but for me, it was JC Penney and Montgomery Ward catalogs.
Must have spend hours in my youth perusing the lingerie/undergarments section.
My crossdressing started with my mom's bra's and slips in the hamper, graduated to taking lingerie/bras from her dresser.
She had one black satin lingerie set that was my favorite to wear when I was home alone.
Another time I found a girdle with garters at my grandmother's when I was staying there that was packed away in the guest bedroom that I took and hid away in my room back home.
That was "purged" along with other things when I went away to college for fear of someone finding my stash.

[LydiaL]

Most of us were crossdressing way before the internet.
Feelings of isolation, confusion and phenomenal pleasure were ever present, but I always thought I was the only crossdresser in the world.
The internet and this website have clearly proven that's not the case!

I agree with much of this. Those of us that live(d) in areas away from the big cities never had opportunities to meet other crossdressers. We were on our own pleasurable journey.

Thanks to the growth of the Internet, I joined a now defunct website and began to interact with other crossdressers and TGs. Crossdressers.com is a great site to get to know and interact with so many others sharing this interest.

[Jessica Secret]

Oh yes, started wearing my mom's romantic lingerie when I was 13 and for several years I did have that identity confusion with myself but by 16 I knew it was who I was and I embraced it. Eventually I went from being straight to bi and badly wanted a boyfriend, which eventually happened.

[Debbie Denier]

Thanks everyone for your replies. The lingerie pages of catelogues appear to have been a major influence growing up. In the UK Freemans and Gratten were the go to catelogues. Probably the first sight of ladies in lingerie for most of us.

[CarlaWestin]

Yup, mom's bras. And then open bottom girdles and stockings. As a young teen I could take the bus into downtown DC and enjoy lingering between the large fabulous display windows at the Dor-Ne Corset Shop.

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[Michelle1955]

Yes, but myself started long before puberty.
By 4 years old best guess.
First item was panties with a friend and I, we were at her house playing in her bedroom.
We ended up switching her panties she was wearing and my underwear I was wearing. Before grade school.
But go back to the Sears, JC Penny catalogs as a young kid before this switching underwear.