What was the first time you wore?

I was eight years old when at last minute went to stay over night at my cousins - I had no clothes with me, but was going going to borrow some old clothes belonging to my older cousin who was also a boy.

When we got to the house and started preparing to go to bed, my Aunt realised that there were no old pyjamas for me to borrow - In the end she said I would have to borrow something to wear from my other cousin who was a girl - I thought she meant pyjamas , but I ended up going to bed in one of her nylon nighties - it felt so silky compared to cotton pj?s I normally wore.

The next morning I even had my breakfast still wearing it.

When I was getting dressed I need some clean underwear and ended up wearing some girls knickers - again felt really nice compared to my y-fronts - I was still wearing them when I got home - unfortunately my mum washed them and gave them back.

I don't recall my exact age. I was very young. My mother use to hang her slips to dry on a clothes line in our apartment. The way the clothes hung to dry made it so any person had to duck and go under the clothesline as you went down the hallway. I discovered the lovely feel of nylon as I brushed by the slips. I would caress and fondle them. There was also a drying rack above the bathtub. When she hanged the slips on the rack I ultimately ended up taking them down and trying them on. I loved the feel of nylon. There was no thoughts of being female. There was no sexual stimulation. That did not occur until puberty.

Over 50. It never occurred to me to try on female clothes before then!:brolleyes:

My sister's coat on Halloween. I was 4.

I was probably 4 or 5. My grandmother had a petticoat (maybe it was a crinoline?). I remember putting it on, but it was probably over my pants. I don't know if my sister and I were playing some kind of dress up? We used to spend the summers with my grandparents. I know I put it on more than once.

I also remember being attracted to the feel and swish of nylon. To this day, I love the feel of nylon.

At 4 or 5 my cousin put her kerchief on me. I don't really remember the first time I put something on by myself. I know it was before I was seven. That was the first time I was caught. I know I had done it before then and gotten away with it.

First time I dressed (albeit about loose a definition of dressed as you can get) came aged 11. I had developed a fascination with skirts over the previous 3 months and had reached the point of having an overwhelming urge to try one for myself.

Fortunately, I have a sister (else who knows what I would have resorted to) and on this particular day everyone else was going to be out of the house. I think my dad might have been at work and my mum and sister going to a parent?s evening at school (not 100% on that).

Anyway, I left it long enough to be sure that no one was going to come back unexpectedly and sneaked into her room to try one of her skirts on. It was a brown skirt with a netted pattern stitched into the outside. Anyway, I knew then that this was an awakening and there would be no going back.

Depends on your definition of first time wearing. If you mean the first time I wore any female clothes, then that was probably when I was 15 or 16 I started wearing what I called 'Male bikinis' under my underwear. I called them that because it was technically made for a guy, but had a panty like style to it. A short time later. Of course I eventually upgraded to actual panties that I managed to buy at work and sneak home. If you mean the first time I went out FULLY dressed, then that would have been in 2018 some time.

I started with my mom's bras and nylons at an early age, maybe as young as 5 years old. I remember dressing up and pretending to be a dancer like one of the Rockettes. I fell in love with the fancy outfits, nylons, sequins, even the large fluffy "tail feathers" they sometimes wore.

I was maybe 12 or 13, my mom's shiny red briefs. Don't know why I first tried them on but I was going through her panty drawer one day and it just felt so natural to take off my clothes and slip into them. It was the first time I masturbated wearing women's clothes. It was an amazing turn on and I was hooked!

My standard answer is that I remember putting on mom's earrings when I was too young to remember anything but there was a big reaction to that and then I didn't do anything like that again until I was old enough to be left home alone.

I always read the stories of people who didn't need to do it until they were 40 or 50 and wonder if that was better or worse? Of course I should have taken more pics when I was younger and maybe cuter but polaroids sucked and digital cameras were hard to come by for some reason.

I do not remember an exact age but I was probably 8 or 9. My mother's old dance leotards, one piece swimsuits, and pantyhose.

i was about 12 or 13 when i first wore one of my mothers old 2 piece bikinis.

Around 5 is the earliest I remember.
I was staying at grandparents' house for the night (unplanned) and grandmother gave me one of her house dresses to wear as PJ's.
I'm not sure that this ACTUALLY the first time, since I have a history of 'borrowing' things from my sister all throughout my childhood. Too many to remember when I started, so I can't say which came first.

I used to go to a Child-minders after school and she had 2 daughters, one 1 year below me, the other 2 years younger than that.
I was about 8 when I got a drink spilled all over me and had no change of clothes, so the Childminder stripped me off and dressed me in pink panties, brown girl's trousers and a pink T shirt. I remember the surprise on my Mum's face when she picked me up and I also remember looking at myself in the full-length mirror when I got home - I stayed in the clothes for a while until just before my Dad got home.

Of course the girls would 'accidentally' spill things on me occasionally after that, those clothes were put aside for me to wear if it happened...Of course I had no real understanding of what was going on inside my head at that time other than it felt good but wrong at the same time.

Just remembered whilst writing this, I stayed overnight once, my parents must have gone away, and I ended up spending all day wearing those clothes for some reason.

The first time I remember: I was 4 or 5, and I couldn't resist getting into my sister's full white petticoat. This was back about 1957 or '58. I still love petticoats.

I was around 11 or 12 and it was at least my moms panties but soon progressed to trying everything and of course loving every minute. Fond memories for sure.

I was five and put on my moms panties and bra been dressing ever since.

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I was 5 my moms panties and bra been dressing ever since.

When I was probably 5 or 6 years old I found and old one piece bathing suit in the attic and for some reason wanted to try it on. I took it and hid it in the woods by our house. A few days later i tried it on and loved how it felt. When I was around 10 I was spending some time at one of my aunt's house and long story short I spent an entire week with her dressed as her niece.

I was 12.

I think I was around 5 when I put on my mothers panties for the first time.

I think I was 10, but if my memory isn't fooling me, 7. The shame crawls on my back.

Next door sisters would play dress up. They invited me to join them. I?m 6-7. Nothing happened until I slipped on a pair of pantyhose. Wow..bells, whistles. I then found Mom?s pantyhose and thigh highs. The rest of the story is obvious.

Somewhere deep in the fog of memory. I remember trying on my sister?s slip. Had to have been before I started school (we didn?t have kindergarten). I remember some comments by siblings about being a house-boy...apparently not being masculine enough at that early age. I perhaps overcompensated in subsequent years, but it didn?t help.

I was 12 or 13 when I first had the urge to put on a skirt of my mother's.

Before long I was also into her panties and bras, girdle and nylons, slips, blouses, dresses, the works!

I'm glad most members responding here are putting their experience into a context or describing their feelings around it. I did try on my mother's nightdress once when I was four or five and it was lying on the bed next to me. And when I was seven my mother dressed me as a woman for a competition--and would you believe, I won first prize! But I don't count those events because they were isolated occurrences and not psychologically significant. The nightdress incident was a mere experiment, done on a whim, and I have no memory of any special feelings associated with it. And it was my mother who instigated the costume incident. More important, neither incident gave me an urge to repeat the behavior in childhood--even if it was rewarded with a prize! But when I put on my mother's skirt at 12 or 13, that's what really got me started crossdressing!

It's a pity we can't do it on this board because we're all crossdressers here, but it would be interesting to survey how many non-crossdressers have put on female clothing at some time in childhood, or had it "put on them." I'm guessing it would be a large percentage. I think we have to have that inner urge to become a permanent crossdresser, and that "first experience" was either a result of that urge, or else just a "trigger" for what followed.

I know I was in elementary school and wore Pantyhose under my pants to school ... not sure on the exact age.

What I don't understand is how a 5 y.o. boy can wear his mom's slip or pantyhose or anything. Aren't they way too big?.

(This same story is in "Heels" thread, elsewhere)

I was in 7th Grade, home alone, reading a cheap paperback in which one of the characters is described as wearing high heels. Pow. I got a pair of my sister's heels and put them on. Haven't stopped since, except when I was caught.

First time I wanted to was at between 5 and 6! A playmate(Lana) threw her dress over her head and I thought that was great and I wanted a dress! Of course,I was a boy and boys don't wear dresses! Early teens was mom's panties! That was the first wearing! Hugs Lana Mae

I was about 10 years old and tried on a pair of my moms black tights (now called leggings). Hooked immediately.

Very early on...but the crowning moment was at 16 when my Aunt took me shopping as Claudine in NYC.....she was a great advocate and instrumental in incorporating my Mother at early age

I don?t remember the exact time but I was a young teenager 13, 14 or maybe as late as 15. But back then girls wore miniskirts to school and by dropping a pencil in class and looking backward, I would be rewarded with a peek of panties. And thinking about what was under those panties was sexually arousing. I also had access to Sears and Penny?s catalogs that showed some lovely lingerie. Well, eventually, I found the laundry hamper where my mother and sister deposited yesterday?s parties. At first, I would just hold and feel the panties as I would take care of business and then the inevitable happened and I put on a pair of nylon briefs. I?ve been hooked ever since.

I was a freshman or sophomore in high school, I was at a thrift store and ran across a dress. I liked it so much, hands shaking I stepped up and bought it. I tried it on that night, it had a side zipper (I hand never seen that before), the dress pulled around me as I zipped it up and fit me perfectly! I looked at myself in the mirror for several minutes, I was hooked!

Growing up we didn't have a cloths dryer so mom would always hang the laundry up in the basement to dry. Since the basement was also my playroom, I had access to bras, girdles, slips .... all hanging there just begging for me to try them on. And try I did and was completely addicted. Mom used to dry her stockings in the bathroom and I would slip them on every chance I got. Absolutely love the feeling.

I was maybe 10 or 11 when I slipped into a pair of fishnet stockings.

My sister dressed me in her ballet tutu when I was about 6. She showed our mother who I remember saying "don't do that - he may want to do it again". Famous last words....

I was 13 when I started. Wore a beautiful foral print dress which felt wonderful.

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!!

I was 10. It was during the school Summer break. We usually stayed at my grandparents, but as I was doing some cycling course in the mornings, I stayed home alone. This was a first.
I was obsessed with tights/pantyhose, and during this time I can recall rummaging through my Mams drawers for some. I liked to touch them. This particular time I pulled them over an arm, then over a leg, then panicked. I put them back and went downstairs. A few minutes later I was back up there, and the urge took over, and there I was standing in front of the mirror wearing my Mams black pantyhose. An electric feel. Over the next few days I repeated this, and also wore a tan pair with heels. I remember wearing a girdle and a slip, but never panties. They seemed a step too far.

I vaguely remember playing with my mother's clothes as a child, but that wasn't really formative or influential. I didn't start seriously crossdressing until much later, in my 50s. I started with a set of lace panties that I would wear all day under boy clothes. Things escalated quickly from there! At first it was for kinky sexual arousal (as my pansexuality awakened) but soon I was dressing just because I liked to. I now consider myself gender-fluid and am trying to hone all aspects of my femininity.

I started very young. I can't remember exactly when it started. I do know that my sister was born one year after me, and I envied the attention my mother gave her. My mother would tell me that I was very clingy and I was jealous of my sister. I have memories as early as 3 years old when I would rummage through my mother's clothes, and enjoy twirling around in slips, skirts, and just about anything I could find. I remember being scolded for it, and telling my parents that I was playing "mommy". I believed that my mother would love me more if I was born a girl. At one point at age 4 my mother made me a dress. I tried it on and immediately started twirling as my mother laughed. My older brother saw me and laughed hysterically. I started crying. My father came in, and put an end to my dress. After that my parents were very strict and put an end to my early crossdressing.

As far back as I can remember around 4 I would play dress up in my mother?s clothes when ever my parents were not around until about 9 then stopped after being caught but at 12 I had a girlfriend that would let me wear her clothes as we were the same size, my happiest memory was dressing in her Girl Scout uniform with her selling Girl Scout cookies door to door. It all ended with my brothers death when one of my dad?s customers after seeing me said To my dad he liked the cookies my sister sold him ( I don?t have a sister).

I was about 10ish dressed with things stored in the attic of the apartment building. and still dressing 60 years later.:hugs:
Angie

I was a sick baby and slept with my Mother when my Dad was away for work from 2 to 5 yrs old.
Mom dressed me in a baby girls satin nightgown and plastic pants.
Mom coddled and pampered me due to my illness of being underdeveloped.
I was there as she got dressed most days.
At that age, I often emulated Mom when she was busy, she was my role model.
I played in her room often with her lingerie, wearing slips, panties, high heels, jewelry, and makeup.
So I was pretty comfortable around silky garments and nice smelling perfumes...reliving my past is just heavenly!

The only thing I recall was I would share room with my sister, she was very messing and she would leave for school before me. One morning I was laying in bed and I couldn't help but notice a pair of biege pantyhose on the floor. I remember grabbing them and putting them on under the sheets in bed and POW! what a feeling. That was great and it starting escalating to skirts and bras but the most amazing moment was the feeling of a slip.

I was around 11 staying at my grans house she was next door and I seen a pair of her yellow silky panties so I picked them up felt so soft as I knew she wouldn't be home for awhile I tried them on just to feel what they felt like and I was hooked been wearing panties for 50 yrs now

I remember being very young and fascinated with my mothers bra. I had one hid behind my chest of drawers when a babysitter found it. I told him that she liked for me to keep them there. HA. Then I would try and girlfriends panties and I love all of the different styles of panties. Now, in my 50' I starting to love womens fashion.

I think I was 12 or 13.
It was one of my mum?s old mini skirts.
It was made of nylon inside and was bright blue outside. I clearly remember it was one or two sizes smaller than mine and that kept my legs really close together. Walking in it was hard but turned me on like nothing else.