Early Teenage Crossdressing Memories

[Michala]

A lot of you have mentioned first wearing your mom's panties or hose. For me the first I remember wearing is my mom's bras. At a young age I already had bigger boobs than all the other boys that I knew my age. Her bra felt so comfortable even though I couldn't completely fill out the cups. Still have man boobs and to this day the most natural item of feminine clothing for is a bra. To bad I don't get a chance to wear them often enough. Wife found one of my bras a few years ago. Didn't overreact but made it clear she had no interest in knowing more. Still in a DADT mode so don't get many chances unless I'm out of town on my own or she's gone for a few days, neither of which happens often.

[Confucius]

I can't remember a time when I wasn't a crossdresser. However when I started school it became clear to me that it was a shameful thing for a boy to do. I know I experienced some gender dysphoria, but I accepted that I was a boy. So there were a few years when I did no crossdressing. However with the advent of puberty I was crossdressing again.

I think I was 11 years old and deep in my mother's closet were some vintage special occasion dresses. I decided on a full slip and a pretty dress, and my body was shaking. I don't think I had the dress on for more than 30 seconds but I was shaking hard and about to explode. I took it off and put it back exactly as I found it. I remember being confused and wondering why did this affected me so powerfully. All I understood was that I really needed to do that again, and again. Soon afterwards I found a newspaper article where a doctor discussed transvestism as a serious mental illness that required electroshock therapy and psychological counseling. That affected my self esteem and I knew that I had to hide my mental illness from the world. No one would ever find out.

[Danielle001]

I started off in my early teens wearing some of my mom's clothes when I got a chance. But when I turned 16 and got my drivers license, I was very excited that I'd get to go to the store by myself and have the opportunity to buy some girly attire. The first place I went was the grocery store of all places. I filled my basket with a few random grocery items and then nervously headed down the hosiery aisle. I always wanted a pair of white tights, so I quickly found a pair, threw them in my basket and bailed to another aisle.

I paid for my items and went home to try on the tights. I quickly found out that in my rush to get out of the hosiery aisle, I actually picked out a pair of little girls tights. They barely went up past my knees!

[Aeslyn]

I have often tried to recall my first and unfortunately I can't. I can recall a few firsts, I just can't recall what order they came in, so which came first. I do recall that I was quite young, seven or eight. I remember I had a lot of girl's things around home as we had a pretty busy house with lots of people around and lots of clothes being left lying around and that I took chances to sneak and wear things often. My best friend who I spent most of my time with was a little girl who lived up the road and we spent a lot of our time playing with dolls and such, which may have been an influence as I may have starting putting girl's things on me as I was often putting them on dolls. And then there were the two 'sisters' I had. Neither were actually related to me though they may as well have been. One only a year older was 'rumoured' to be my father's daughter, but that is unlikely. We bathed together often when we were younger though and I do remember finding excuses to stay back in the washroom after our baths to wear the clothes she'd left behind. And then the older of these two sisters was a girl my parents took in after her mother abandoned her when she was twelve. She was much older than I was and in her mid to late teens when I was seven or eight she had her own apartment. I used to visit her at her place often and I remember one time that something had happened to my clothes and I couldn't wear my shirt home. It was a small town so even at that age I was allowed to go places alone. I remember clearly the walk home in one of her long sleeve pink shirts with a pink bow at the front of the neck. I was both excited and frightened.
I do remember all these things quite clearly, the only part I cannot remember is which came first.

[MarinaTwelve200]

My story is a bit unusual----When I was a kid in the late 50s and early 60s I became "interested" or even a bit "fearful" of the thick red lipstick worn by my mother , her friends and the teenage girls that attended the consolidated school I went to. I thought I would be kissed and would not be able to get it off. And my classmates told me of how the "Leather Jacket" teens would sometimes accost one of us younger kids at the drug store or bathrooms and force lipstick on their victim, just for fun.--Fortunately, I had a close call or two, but got away. However, I think the Trigger incident happened at age eight. when I was washing my hands at home, in the bathroom, and mom came in to use the mirror to put on her lipstick. My hesitation caught her attention and she joked "Do you want me to put lipstick on YOU too?" NOOO, I said and walked towards the door. She thought my reaction was amusing, and got an idea "TOM!" she called out to my father "Come hold Marty while I put some lipstick on him"--A made a dash for the Bathroom door---Too Late! Laughing, my father grabbed me, and managed to hold me in place and my head still.---I couldn't move! Mom approached me with the open red lipstick tube, and holding her mouth, sort of open, like, I supposed she wanted me to do. But just when she got about an inch or so away, she backed off. "Go ahead", my father told her. "I don't know, it might give him a complex", and to my relief put the lipstick away. I wasted no time getting out of there. However, though, since then I sort of became obsessed with the concept of having to wear red lipstick---but was frightened it wouldn't come off. When I was twelve, I finally got brave when I was left home by myself for the day. I opened the lipstick and put a small spot on my arm. Then wiped it with some paper---It came OFF! then I actually tried it on my lips. I really got a "Charge" out of it. So for the next year or so I would try it every time I had a few hours alone.---Eventually about age 13, I was alone, and decided to go full bore. I borrowed mom's clothing, which was my size (or a tad bigger), from the laundry.---Bra, Panties, slip, girdle and nylons, and of course, Lipstick.-------And I was hooked from then on.

Still, I often wondered what would have happened Had my mother had actually put the lipstick on me back then.-----Would I have discovered all my fears about it were unfounded?---and would it have lost it's power over me?---Would I have gone on the way I did, eventually graduating to full CD, or have lost my fascination with it and the CD never starting.

[sami1952]

I was in the seven grade when I started crossdressing, used to wear my moms bras and panties then started with my younger sister's clothes they fitted a lot better then my moms. back then it was more sexual then just dressing up. started dressing fully after my wife found my stash, glad she did cause it open the door for me to dress up without having to hide from it. I've gone a long way since those early days.

[AllieBellema]

My grandma had enough clothes in the closet to start her own K-Mart... literally. So whenever my grandparents were away, I spent time digging through her closet to find things that interest me. I even pulled some stuff and kept it in my own closet. I also managed to convince my grandpa to let me use his CC to buy myself a southern belle dress for halloween (he was easy going and I'm not sure how he let me get away with that!). My family never found out either... well, as far as I knew. When I got ready to move to Indiana, I managed to put all the clothes back in the closet, which was easy since it was mostly in garbage bags anyway and I sealed up the southern belle dress and wrote "Halloween Costume" and put it in another closet separate from mine. Nobody ever questioned me about that and I never knew what happened to that.

I ended up taking a hiatus from crossdressing for several years before the urge came back strong.

[Ozark]

I was around 9 years old.

My 15 year old cousin had moved in with us. It was a sad story, her mother had died, her father remarried, the typical wicked step mother, heart attack and her father died and the step mother went into a nursing home.

Somehow in my 9 year old mind, I thought she (the cousin) was getting favorable treatment from my parents. I wanted to get the same kind of treatment.

For some reason I thought if I wore her clothes, my parents and grandparents would shower me with affection also.

I put on a pair of her yellow big panties (this was about 1958) and a pair of her side zip jeans. Nobody even noticed. (In retrospect I don't see how they could not have known, but they didn't say anything to me at the time.)

One time when my parents went on a trip and the cousin was in charge of us. She was downstairs reading a book. I got on a pair of her panties and crawled into her bed. (In our house it was scandalous to sleep in anything but pajamas or a nightgown.)

The cousin came upstairs and turned on the light in her bedroom and saw me in her bed. I feigned being asleep. She came over and ever so gently lifted up the covers and saw me in her panties. The covers came back down, she turned out the light and went and got into my bed.

After a while, I went into my bedroom in just her panties. She was in my bed reading a book. I told her I was scared and wanted someone to hold me. She looked at me and told me to go back to bed and hold myself.

The episode was never mentioned again.

She eventually went away to college.

Fast forward about 5 or 6 years. I had developed a bedwetting problem. Wet beds and wet sheets were a real bummer.

My father insisted I was just to d*** lazy to get out of the bed to go to the bathroom. Lots of tears, spankings and wet pajamas. My mother eventually bought me several pairs of 'stay dry' incontinent pants that I was to wear under my pajamas. I was both embarassed and excited about them at the same time.

My father had remodeled our basement and turned it into a bedroom. I was down there by myself, had a tv and radio and my school desk where I did my homework.

I had progressed to buying my own panties by this time.---this was before walmart and kmart. Went to Kresgee's or Woolworths to get them.

One night I was in bed in a just a pair of panties.

My mother came downstairs to kiss me goodnight. My pajamas were lying on my desk, along with some laundry she had told me to put away earlier in the day.

She told me to get out of bed and put away the laundry like she had told me to do. I told her no, could I do it in the morning, I was tired.

Mother insisted I do as she told me to do. Then she saw my pajamas and wanted to know why I didn't have them on and did I have on my 'protection' (That was our code word for the incontinent pants and diapers I wore to bed....we would NEVER call them by their real names, only by protection.)

Mother than told me to get out of bed right now. I refused. She reached down to pull my covers off of me and I blurted out, "Mom, I'm naked!"

She went over to my desk and picked up my pajama bottoms, gave them to me and told me put them on and put away the laundry.

I put the bottoms on over my panties while still under the covers and got out of bed and started to put away my laundry. She then insisted I wear protection to bed and I was always to wear protection and pajamas to bed. Nice people didn't sleep without pajamas.

She then swatted my butt. She must have been able to tell I had something on under my pajamas because she pulled out the waistband and asked me what I was wearing.

I started crying. I told her it wasn't fair, I hated wearing protection, I hated having to wear big white briefs (JC Penny double seats--wish I had some now..she bought them for me) that looked like diapers, I hated wearing diapers to bed and I liked how these underpants felt. I told her I had bought them thinking they were boy's bikini underpants.

She hugged me and said she understood how I felt. But until I outgrew the bedwetting it was so much easier on her to have me wear protection. It was too much trouble to have to laundry everyday--we didn't have a dryer- and to wipe my face and put on my protection and go to bed.

And she stood there. I didn't know what I was supposed to do. I was too embarassed to pull of my pajama pants and have my mother see me in panties. I had only occasionally put on my protection in front of her, never in front of my father.

Finally I said the heck with it, sat on the bed and took of my pajama bottoms. I then walked over to my desk in my panties and turned my back, took off the panties and pulled on my protection.

This was very exciting to me and I didn't know why.

I started to get back into bed and my mother asked if I was forgetting something. I started to put on the pajama bottoms. No, my mother said, finish putting away the laundry.

I put away the laundry in my chest of drawers just wearing my protection. I was so embarassed and excited at the same time and didn't know why.

When I was done, my mother came over and kissed me and said, 'don't forget your pajamas." and went out the door and turned out the light.

Oh man, I knew I was in trouble. Not only was I a bedwetter, but my Mom had found out I wear panties. And she was probably going to tell my dad. I worried about that until I fell asleep. I think I cried myself to sleep that night. I wished I had on panties instead of protection.

The next day when I got home from school, I was in my basement room lying on my bed watching TV. My mom came downstairs with a bag from Sears.

She sat on my bed and said she loved me and was so proud of me for being a nice young man. She told me she was sorry that I struggled so much. She knew I was a good kid. Things will get better she said. Then, as she leaned over and hugged me, she said, "I understand boys need their privacy," and handed me the bag. "These are for you", she said.

Somehow I knew I had the upper hand. I just laid there and didn't return her hug or take the bag. She got up, left the bag on my bed, said supper will be ready when your father gets home and went upstairs. At the top of the stairs, she turned and said to me, "I am not going to mention this to your father."

After a while, I looked in the bag. There was a package of panties, Sear's VIP hipster panties, three pair, blue, yellow and white.

[Georgina]

Whenever I became a teenager I already knew about the delights of a female wardrobe. As my sisters were younger than me I had to search my mother's closet for items to wear. I was lucky this was during the golden era of lingerie, as my love of girdles, stockings and slips began back then. My lasting memory of that period was wanting all the lovely items available in the many catalogues and not being able to afford them. I promised myself, one day, I would have my own and I kept my promise.

[CaseyAdams]

When I was in third or fourth grade, going to a sleepover where one of the girls suggested trading underware. It was very comfortable and probably lead to the spark of my crossdressing, but it is difficult to say I wouldn't have become trans if that didn't happen. I remember being mistaken for a girl different times around the same age and didn't have any problem with it.

[Jamie390]

Like so many others, I started with my mom's bras, panties, pantyhose nighties etc. But, I especially liked her purple bathing suit. I'd wear it in the shower sometimes, then hang it in the attic, out of sight to dry. One day, I came home, and my mom and dad were cleaning out the attic. I noticed the wet bathing suit on the attic steps. One of them obviously saw it and set it on the steps to bring downstairs. Neither one of them ever mentioned it though.

[njcddresser]

For me it was wearing my older sisters bra and panties when I was 14. I quickly developed a fascination with lingerie. I had a girlfriend when would let me wear her panties when we were messing around. When I got to college I began to put together a small collection of panties. At this time I had a fascination with garters and stockings. When Home on Christmas break I bought myself a teddie that had garters. I couldn’t wait to get back to school put it on.

Fast forward 35 years, I still love lingerie and now wear panties exclusively. My favorites being high cut satin bikinis. I still love garters and stockings!,

[Amanda1963]

I was around 14 when I started wearing my aunt's panties and bras. she is 4 days older than me and I would sneak into her bedroom and go through her lingerie drawer and "borrow" items. she also had stockings and garters that I loved wearing. I remember one night i put on bra and panties along with the garter and stockings and ended up falling asleep. the next morning my dad came in to tell me to get up and fortunately I had the blanket pulled up around my neck and he didn't see what I was wearing!!

[Foxy Lady]

I was about ten and tried on mom's Playtex OBG nylons bra a nd panties and was hooked. Iam now 75 and still dress daily.

[Thumbelina]

First time for me; Sister's panties. I was a Freshman in high school (1977) and wore my sister's pretty pink panties to school one day under my tight Levi's 501s. It's one of those things I'll always remember.

[Asew]

My sister got a pink poodle skirt for halloween (this was the 90s) and it was my absolute favorite skirt I have ever worn. Thinking about it makes me want to buy one now

[Glenda58]

Mom was a girl scout troop leader. As the girls would grow up or leave the troop they would give my mother their uniforms to give to new girls coming into the troop. There were skirts and blouses and sometimes slips. When mom was away during the day I would go into her storage place of uniforms and try them on. I use my mothers panties and hose and dress till I knew she coming home. Did this till I was 14.

[IleneD]

I had a period prior to puberty around age 11 or 12 when I had a pair of Mom's panties that I would wear under the bed covers. The habit didn't last long and faded.
I grew up a "sissy", and was constantly reminded of my lack of boyhood manliness. Awkward, slightly effeminate, nerdish and bookish. Always had girly feelings but never understood them. You know that kid.

The REAL first time en femme was in high school. It was a huge eye opener too.
I played HS football. (Yes, scrawny at the time Me; at the literal threats of my dad to make a man of me). At the end of the season the school held a Powder Puff football game in which the girls and female cheerleaders would assume the role of players, and the men/players would assume the role of cheerleaders and the "homecoming queen & court" for the evening dance mixer.
I was selected to be one of the contestants for Powder Puff Queen. The girls of my HS made the nominations, BTW. I was no ladies man at the time, so make your own conclusions here. For the ball we had to dress as girls and ball queens.
The other boys who were contestants came dressed more as clown versions of women; caricatures. BUT.... my mother (God bless her) actually took the assignment seriously. She helped dress me for the ball, and she did so in earnest making me quite pretty. Not clownish or silly at all. She had a gold lame' long dress she gave me; a wig and of course her makeup. The works. There's a (bad) picture in my yearbook of me in my first feminine glory.

Oh... I was crowned as Powder Puff Queen.


The most stunning part wasn't just that I was PRETTY in person for the very first fascinating time, but I discovered that I was a dead ringer for my mother (when she was about my same age). My Mom was a beautiful woman too. But that image of ME as my mom, and me loving it has lasted with me all these years.

[Cherylgyno]

First time I was 6 year's old. I wore Mom's clothes. Mom knew from day one. Luckily she never told anyone.

[ShyLibrarian]

I had a period prior to puberty around age 11 or 12 when I had a pair of Mom's panties that I would wear under the bed covers. The habit didn't last long and faded.
I grew up a "sissy", and was constantly reminded of my lack of boyhood manliness. Awkward, slightly effeminate, nerdish and bookish. Always had girly feelings but never understood them. You know that kid.

The REAL first time en femme was in high school. It was a huge eye opener too.
I played HS football. (Yes, scrawny at the time Me; at the literal threats of my dad to make a man of me). At the end of the season the school held a Powder Puff football game in which the girls and female cheerleaders would assume the role of players, and the men/players would assume the role of cheerleaders and the "homecoming queen & court" for the evening dance mixer.
I was selected to be one of the contestants for Powder Puff Queen. The girls of my HS made the nominations, BTW. I was no ladies man at the time, so make your own conclusions here. For the ball we had to dress as girls and ball queens.
The other boys who were contestants came dressed more as clown versions of women; caricatures. BUT.... my mother (God bless her) actually took the assignment seriously. She helped dress me for the ball, and she did so in earnest making me quite pretty. Not clownish or silly at all. She had a gold lame' long dress she gave me; a wig and of course her makeup. The works. There's a (bad) picture in my yearbook of me in my first feminine glory.

Oh... I was crowned as Powder Puff Queen.


The most stunning part wasn't just that I was PRETTY in person for the very first fascinating time, but I discovered that I was a dead ringer for my mother (when she was about my same age). My Mom was a beautiful woman too. But that image of ME as my mom, and me loving it has lasted with me all these years.

My first wife's father was also in the 'make a man out of you yet' brigade and shamed her brother (artist/painter) into going to Vietnam, where he soon succumbed to friendly fire and is buried in Pleasantville NY. However, she was very close to her father and although aware of her brother's loss and grieving it from time to time, remained his number one fan.

He'd been a fighter pilot in the Pacific theatre/theater in WW and was a likeable guy, but I was always a bit put off by him - I suppose for precisely that reason.

I wasn't really an active cross dresser in high school (the odd spate of panty wearing), but like you I was an inveterate reader and certainly no jock and tended to hang out with guys who were bright and relatively non-aggressive. The cross dressing kicked in late 30s.

Thanks for your informative post, Ilene

[wanda66]

haveing all brothers and no sisters my Mom was my only female reference. Growing up there was always reference to “ looking sexy “ .So when I was able to try on Mons bra and panties ,I felt SEXY. But I had to be man sexy also. So that’s how things were and are .

[helenejo]

My mum used to wear those frilly blouses with the high collars like Lady Di used to wear. I thought she was so beautiful and used to borrow them so I could look like Lady Di too. I remember a cream silk one with a big bow at the ruffle neck and a grey one..happy memories

[Karmen]

I always sneaked up in mom's closet when I was home alone and wore her old dresses or skirts, because she was thinner when she was younger. And also walked around the house in her heels until my feet were not too big for them. I just wonder if she ever noticed some of her shoes got more and more worn out even she never wore them.

[sometimes_miss]

It wasn't my mom's stuff, it was my older sister's. She being six feet tall by the time she was 16, there was always lots of out of fashion stuff that she would no longer wear (relegated to the back of the closet or stored in the attic), so I did.

[sara66]

My sister was a little goth. But she had great taste and most dresses and skirts were short. Even though she was a couple years younger we were almost always the same size, Nothing in her closet was safe. I whis she had bigger feet. The only time she was smaller was she was a senior in HS. She dropped to a size 10, so I missed out on a great prom dress.
Sara