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

[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.