Early Teenage Crossdressing Memories

[dawn459]

My earliest teenage Crossdressing memories started with my MoMs panties
And hose and progressed from their to my first pair of sexy blue bikini panties
That I took out of the girls locker room when I was manager It was my responsibility to make sure the lights
And the showers were all off laying in the
Floor in front of the lockers was the panties I picked them up put them in my
Pocket brought them home& wore them
At night & hid them under my pillow &mattress well one morning mom goes
To change my sheets to wash moves the
Pillow& finds the panties she never said anything to me so one day a buddy of mine&I along with his mom were together over at his home and our mom's
Were talking about finding magazines under his mattress mom said she hadn't found any magazines but had found a pair of panties under my pillow.She knew
That they were not hers but She knew that I was wearing the panties.
So that started my lingerie wearing
Which has turned into full crossdressing.

[Jodie_Lynn]

that must have been a helluva embarrassing conversation!

[Kendalli]

That's a crappy way of being outed. When my parents found me wearing women's clothing, as embarrassing and humiliating my mother made it, at least she kept it within the family. At least as far as I know.

[DIANEF]

My mums stuff was too big for me to wear, but her shoes did fit, plus I had an older sister and her clothes fitted me perfectly. Once my mum found her shoes in my bedroom, I blamed my brother for putting them there, but I'm pretty sure she knew the real reason.

[alwayshave]

I was not allowed in my parents room so it was hard to wear mom's stuff, but I did have older sisters.

[DaisyLawrence]

I never was able to wear my mums clothes because she was, um, dead. I was a small 10 year old kid when it happened and far to small to get into any of her clothes (I could have gone camping the her bras) but I used to look at them in her closet and they reminded me of her. They were the only things in the house that were exclusively hers. I would sit with an item of clothing in my hands and I swear I could smell her. Then, a few months after her death my dad had a breakdown and through away everything that reminded him of her thinking it would help. All the clothes went along with the trigger to my childhood memories. 43 years later and the memories are almost all gone. Life can s**t on you sometimes. I did have an older sister but wearing her clothes would have felt weird so my teenage crossdressing was in my head rather than in real life. Making up for it now :)

[AlissaMurray]

I'm guilty of the Mom thing. It all started for me with a nylon body suit shirt, it was red and to this day I look for one like it but as of now no luck yet. It was a 70's style thing but maybe one day one will show up at my local 2nd hand store. From there it progressed to pantie hose, nylon panties and my cousins one piece bathing suits. I come from 5 boys me being the oldest, I sure loved when my girl cousins came to visit.

[Monique65]

I, like so many others, first started with my mother's girdles and hose. I had an older sister as well, and would sneak into her room and try on her skirts, dresses, bras and panties. I came very close to being caught by my mother one time. I was in my sister's room modeling her stockings and heels when I heard my mother coming up the stairs. I quickly and clumsily ran across the landing into my room, losing a heel on the way. I was sitting on my bed as my mother entered, and I slid my still stockinged and heeled leg as far under my bed as I could. She looked at me, laid down the clothes she was carrying, and turned to leave without saying a word.

We never spoke of the incident, but I'm sure she saw the other heel lying outside my door and wondered.

[Rollermiss]

My first dressing was my skating partners competition costume. I must have been 11. I had always loved the way she looked in it. One day her and her Mom picked me up for practice. It was laying in a box with other cloths. I asked what is with all the cloths. Her mom said they where going to the thrift store as we recently changed out costumes. Embarrassing as it was I bought it from the store, maybe as a remembrance. One day I put it on to just kind of see. I was hooked. Then it snowballed to what about panties under it, and a bra, and so on.

Kelsey

[Jaylyn]

Moms stockings that had runners and her old girdles with the garters she threw out and mom letting me play dress up in her things. She even painted my toe and finger nails sometimes when she was painting hers. She had wanted a girl so bad I guess she thought she was gonna make me into one. I have an old black n white picture of me in a dress she sewed out of flour sacks. ( for all you youngsters flour used to come in cloth flowered colored sacks in about 25 pound sacks) mom let my hair grow and even put a bow in it for the picture. Dad finally put a stop to that but I'm thinking the damage had already been done.... Lol

[Denise S]

My crossdressing began by being curious about my sisters dance recital costumes. They were so pretty and feminine bright metallic satin lace and finge. I slipped the first one on and was hooked, the way it felt and looked was amazing. My sisters also had drawers full of leotards, tights, dance skirts that I loved. I remember, that I couldn’t wait for school to end so I could get home and try on all these wonderful clothes. My dressing expanded to panties bras dresses anything fem. it’s funny to think back then all my friends were going to play basketball or football after school and a lot of times I would tell them I couldn’t because I secretly wanted to go home and practice being a bellarinia. I wish I had the internet back then, as I thought I was the only boy wearing girls clothing.

[NancySue]

Sisters, who lived next door, often played “dress up”. One day, they asked me I’d like to play too. For some reason, I said “yes”. When they helped me put nylon stockings on, I was hooked...to this day. I, then got into moms stockings causing an occasional run, but she never said anything. She wore garter belts and nylons. Things naturally progressed. I wear all forms of hose, but definitely favor nylons and garter belts. Nice memories.

[gunta]

When I started crossdressing at my middle teenage I was lucky because had quiet older sister, I tried almoust everything and never get cought :). I was precautious, shower before, remember exact places I take stuff etc. But slowly I grew up and size didn't fit anymore :(

[Christie ann]

Mom was quite the square dancer and she had dozens of those dresses with petticoats. After school was a fun time.

[Lea]

I started before my teenage years. When I was in my teen age years my parents worked second shift so I was home alone.
I would raid my moms closet for her dresses and skirts. I wore her girdles and shoes.

[Rachael Leigh]

My moms panties were also my first item of ladies wear and then I tried on a green dress. Yes for me that’s what got me started, I felt guilty but somehow it just felt right to me.

[Josie Whimwham]

I used to rescue my mom's old pantyhose from the garbage to just try on.
Of course, being a brilliant 11 year old, I "hid" them in my sock drawer, and of course she found them.
She got a bit irate and asked, "What are these doing here?!!" I brilliantly responded "I don't know."

Later I would borrow my sisters clothes for a few fun hours and luckily never got caught--although I'm pretty sure mom knew something was up with me.

[Stephanie47]

If I were the mom and found a pair of panties under my son's pillow I'd wonder if the panties were not a "trophy" given to him by a girl.

[Karen RHT]

What I recall most about being a crossdresser when I got to my teens, was learning about the ignorant and brutal prejudice directed towards us at the time. So much misunderstanding, misconception, fear, and loathing directed towards us. Keep in mind I turned 14 in 1961. Very different times, in many different ways.


Karen

[Jaymees22]

My teenage dressing was my mom's LBD, pantyhose and a blond wig she had. I was quite aroused even though I wasn't pleased with the way I looked. I had bushy eyebrows and hairy legs not too attractive. I really only remember doing it a couple of times at that age.

[Rebecca60]

I would’ve blushed for days if mom let the cat out of the bag. For me it was an older sister, I would wear her panties and silky night gowns

[SarahMarie]

My first time I was younger than a teenager but the most remember able time as a teenager was a game of Truth Or Dare with my best friend (GG), my sister and mom. I picked dare and best friend dared me to wear a dress (one of hers). I accepted the dare and she dressed me up and even made me go out side. If only I had told them then.

[dana digs sweaters]

Just a continuation of wearing my sister's and mother's clothes since I was 7.
Having 5 sisters growing up gave me quite the selection to choose from.
Oh the burden I had to bear :daydreaming:

[Lacey New]

Like many of us, I started with Mom's panties. I also had a sister a year younger and I would borrow hers as well. I would "borrow" them for a few minutes, head to the bathroom, lock the door, take care of business and return them to where I found them. As time went on, I would "borrow" anything else that was available as well, a bra or a slip for the most part - occasionally stockings. I don't know at what point I was "hooked" but since I kept on doing the same thing and now have been dressing for many years, I guess it was from that first time putting on panties in my early teens.

[Stephanie Julianna]

Before I was a teen I was trying on some of my mom's stockings, lingerie and dresses. She was only 5'1" so we were not far apart in size. However, I was also the same size as my sister at 5 feet. She had graduated from high school in 1958 and had worn an incredible tea length strapless gown to her prom that I simply adored. It had a pale lime green lace covered satin bodice with a wide satin swatch around the waist. The skirt was white chiffon over the green satin with tulle underskirt. She wore it withe two bouffant petticoats that made it stand out dramatically. the hem was just above the ankles. I spent hours in that dress. I remember my sister in it going to the prom and thought she looked like a princess. I was eleven at the time. That prom was also the first time that my sister and brother-in-law met. He was the date of another girl at the time. He was even charmed by her look and to this day still calls that gown the "ZAP" dress because that was what she was wearing when he fell for her. The power of that perfect dress started an affair that is now in its 58th year of marriage.

[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.:heehee:
Sara

[lynda]

Hi girls I started dressing very young with my mom stuff but I was lucky my mom caught me in her girdle she came home early from work and caught me she told me she didn't care about dressing up but not in her clothes so she took me to JCPenney's and pour me some my own clothes to where she said she was not going to tell my father cuz he wouldn't understand so every night when my father went to work it worked from 7 to 7 all night my mom will let me dress I just love my mom until the day she passed we were close friends I think she enjoyed having a little girl sometimes

[KelleyB]

By the time I was 12-13, when my sister and I visited my mother at her apartment (divorced parents, father got custody), I'd always do my utmost to stay home when they went out shopping or whatever.

It was during these times I explored my mother's half slips, bras, and a few dresses/skirts. I've just recently gotten back into wearing dresses/skirts along with bras, blouses, and half slips. My wife is just fine with it, as "they're just clothes". I was quite relieved, as she'd never seen me dressed to that degree until last year.

[Susan Thomas]

My experience is very similar to the other girls. I was about eleven or twelve and found myself attracted to my fifteen year old sister's one-piece swimsuit. After trying on the swimsuit, I progressed to her panties and bra. The trigger for my crossdressing might have been an incident that happened on our vacation, a month earlier. We were in Ontario, Canada at a cottage on a lake. I was playing with my cousins in the yard and then out of the blue, my aunt and uncle (for an unknown reason) held me down and put a bra on me. I still remember it was a white padded bra. My aunt took a picture of me wearing the bra. Years later, she sent me a copy of the picture. I really do look quite upset. I always wonder if I would have become a crossdresser if not for being forced to wear that bra. I suppose most boys would have just laughed it off, so maybe I had a feminine side that waiting to be awakend.

As far as my pre-teen crossdressing, it only lasted a few weeks. I was in my sister's bedroom, admiring my refection in the mirror. The red one-piece swimsuit just seemed so right and I felt so feminine. Unfortunately, I had lost track of time and my mom returned home way sooner that I was expecting. I was caught red-handed. She started yelling at me and asking me if I wanted to be a girl. Nothing else was said and I don't think that she told my dad or my sister. I must have been quite frightened, because I didn't again crossdress for ten years. I am still in the closet, but I have managed to have a happy marriage as well a nice career as a military and airline pilot.

[Sporco]

I remember playing "dress up" when I was 7 or 8. I'm not sure how it got started but dress up involved some of my mom's satin briefs in bright colors. At some point that stopped. I really didn't think much about it until just now.

Then when I was 12 I found a pair of girls forest green cable knit knee high socks. I had developed quite an interest in feminine socks so getting a chance to actually wear them had my heart racing.

Then at 14 I found a pair of black pantyhose at school and tried them on. The hook was fully set with this. I remember riding my bike to the pharmacy to buy pantyhose of my own after that and wore them under my pants to school pretty much all the time unless I had gym that day.

I've been dressing underneath ever since. I still love girly socks and hosiery, but also panties, lingerie and pretty much any other feminine clothing. I wish I looked better in it, but I still enjoy it.

[Vintage4sarah]

I was fascinated with my mother's nylons from an early age and that would extend to my sister and my other close relatives. The problem occurred that by 13 years old I was nearly 6' tall and my mom was 4'11" and my sister 5'3". Nothing really fit as I desired the opportunity to go beyond just wearing nylons.

At 14, I started to dog sit for neighbors who left on vacations. The moment would come when I starting sitting for neighbors where both the mom and her daughter were taller, especially the daughter. Everything lined up one day when I toke the leap and I was able to completely done their stuff from the girdle and bra to skirts, tops, nylons and shoes to fully become the image of a female. That first time viewing me in the mirror was electrifying. The next day, I snuck out of our house with a hair piece of my sister's. This time the image in the mirror was a true revelation of my potential. There was some guilt with this, but this only made me more cautious and looking for more opportunities.

More sitting jobs would follow until I left to attend university not to be relived until well into my mature years when it all fell in place once more.