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I’ll never ever forget my very first cross dressing experience! I remember every detail as though it happened just yesterday!
I was nine years old and in the fourth grade at our junior high school, which went from first grade all the way through the ninth grade. I would walk to and from school each day with at least four buddies of mine from our neighborhood. It was a hike through a long field and then some tall woods. It was about a half-a-mile hike each way to and from school.
It was a rare day because none of us had city league football practice that day. My mom and two sisters had just left for a long Girl Scout meeting. My dad wouldn’t be home from work until at least 6:30 pm. So, I had the entire house to myself for at least two and a half hours.
For some reason that day I felt an urge to start snooping around in a place that was always totally off limits to us kids – my mom and dad’s bedroom. My mom had two chests of drawers in that bedroom, and I started rifling through them. The first set of her dresser drawers had nothing interesting in it to me, so I went to the second set of drawers.
I hit that jackpot when I got to the bottom two drawers! They were full of nothing but piles and piles of sexy black lingerie! Black garter belts, shear black panties, a pile of jet black silk thigh high hose, and sexy shear black bras. Both drawers were loaded with the sexiest clothing items I had ever seen in my life and all black. It was apparent my dad liked to make love to my mom while she was wearing a black set of these goodies. I must have picked up that same gene from my dad because I always have my wife dressed up in all of that sexy stuff for our bedroom adventures.
I pull out a set of the sexy items from the next to bottom drawer – a black garter belt, a pair of jet black thigh high hose, a black shear pair of panties, and a shear black bra and lay everything out neatly on the bed in the order I was going to put them on. First was going to be the panties followed by the sexy bra and then the garter belt and those gorgeous jet black silk thigh high hose.
However, before getting all dolled up in that sexy black ensemble, I decided to look for a pair of black heels in the closet to go with the outfit and while moving everything around in the bottom of that closet, I found a stack of my dad’s Playboy magazines. Wow, I just hit my second jackpot! I pulled the top six magazines out and opened them up to the centerfolds in each magazine. After I found those Playboys, I didn’t even bother looking any further for those black heels.
After laying out six of the Playboy magazines opened to the centerfolds of the magazines and placing them where I wanted them on the bed, it was time to put on all of that sexy black lingerie in the order noted above. Each piece of the black lingerie felt amazing up against my skin! The last part, which was a bit challenging for the first time trying it, was hooking all four garter belt straps to the hose from the garter belt in just the perfect position they were supposed to be in. I hopped up on that bed with my head surrounded by all of those Playboy centerfolds (and you know how this part goes.) I was in adolescent heaven. I was careful of my mom’s sexy black lingerie and their bed to leave no trace behind of me being there!
I just laid there in a blissful fog for about a half an hour before I started putting everything I pulled out right back where I found it.
Girlfriends, that was my very first cross dressing experience and now you know how I got hooked on cross dressing and could never give it up to this very day!
Girls, thanks for taking time to read my article about my very first cross dressing experience. Please feel free to comment on my article or answer one or more of the following questions:
* When you had your first cross dressing experience, what femme clothing items did you put on?
* Did you then (if you started when you were younger) or still today find dressing to be arousing or do you dress for other reasons now?
* How old were you the first time you ever cross dressed and did anyone in your immediate family ever catch you in the act of cross dressing?
Thank you girls for reading my article and my questions. I look forward to all of your responses!
Sincerely, Scarlett
More Articles by Scarlett398
- Scarlett’s Purpose at Crossdresser Heaven!
- A Few Of Scarlett’s Hot Tips On Fashion And Beauty!
- “Scarlett’s Hot Tips On Photo Shoots!”
- Scarlett On Having “The Talk” With Your Wife Or SO
- Scarlett On How To Share Your Thrill Of Cross Dressing With Others
Scarlett, My first time crossdressing was when I was 11 or 12. I was snooping in my moms drawers and found one of her bikini bathing suits. Since it was Spring, she wouldn’t miss it so I tried it on and immediately I felt the sense that this is what I want to wear. I kept it hidden in my room until she found it one day. After laying on the best lies I could think of, she took it back and could only visit it in her drawer. Still, I remember it so clearly.
Marlie
Thanks for sharing the first femme clothing you scooped up out of one of your mother’s dresser drawers, Marlie.
That must have been an exciting feeling putting on a bikini bathing suit as your first femme item of clothing to wear!
Scarlett
It was too small but it opened the door to my new favorite lifestyle.
Marlie
Good for you Marlie!
Scarlett
Thanks for describing your first CD experience. 
My earliest experiences were with a pale green full slip and silky nightdresses.
It’s interesting to find out how others started; Its fascinating how we may start on underwear only and at a certain point it becomes something more and we develop over time into our female persona and fully dressed look.
I think that’s the way most of us start and finish!
Thank you Alicen!…..Scarlett 
Thank you for sharing your first experience. I was ten years old with too much time on my hands. As a middle child of a family of seven, I learned that being overlooked had its advantages. I was always fascinated by the clothes that girls wore, so I used to snoop around my sister’s clothes until one afternoon I found a full satin slip with lace on the borders and on the straps. It was a shiny pearl white color. I put it on in my sister’s room when everyone was home. I was too young to know if I… Read more »
Thanks for sending in your response and with that many folks around the house, Rose, I’m surprised you never got caught!
Scarlett 
I think innocently many of us start with lingerie and I think it’s quite normal for a young developing boy to get aroused over the silkiness of the fabrics. I certainly know I did! I don’t think it’s uncommon for many men to have gone through this stage. There is a difference between those young boys who discovered something that gave them sexual arousal and those of us who had strong desires to take it beyond the fetish stage of wearing lingerie for the sole purpose of sexual gratification. My greatest pleasures are getting fully dressed as a girl and… Read more »
Scarlett I was a boy in a house with five girls my youngest sister dressed me in her panties and a little dress when I was 10 years old and I was hooked .My oldest sister and wife soon to be caught us it was hard for them to understand that we would do this together thought it was wrong it’s been a long road but life is great now my wife has been very understanding finally and now we dress up as much as possible
Good for you Jerri and so happy to hear you have such an accepting and understanding wife who even participates with your thrill of cross dressing. My wife is accepting now however with a couple of limits. I can’t be dressed as Scarlett while in her presence. She says it would be such a romantic turn off to her and she much prefers me in what she calls my “Handsome Husband" mode. She hasn’t got a lesbain bone in her body so my fantasy of wanting to make love to her with me being dressed up as Scarlett will have… Read more »
Thank you Scarlett I am very lucky I love my wife very much she is so helpful and open she had problems with my youngest sister but realized that we just enjoy dressing up and have fun and still do when we can but just when my wife is ok with us . You are a very beautiful girl love your photos unbelievably beautiful and a great role model.
Thank you Jerri
No…it’s thank you Jerri for such a wonderful and sweet note. An early happy Easter to you and your family!
XOXOXO Scarlett
Hi, Scarlett. Loved the recounting of your first time crossdressing. It’s always fascinating to hear how other girls began this wonderful journey. I first succumbed to the urge, which I first detected when I was five or so, to crossdress at the age of 12. We had a very stylish and young roomer named Eva who occupied the room across from mine on the third floor of our house. One day I finally gathered the temerity to go into her room and open her chest of drawers. I found a silk and lace slip that I just had to put… Read more »
Good for you Petra sounds like you’re pretty stealthy with your cross dressing. I had to be like that for years and years! Glad that stage of my cross dressing is long gone. I never have to hide anything anymore, however, I can’t be dressed as Scarlett while in my wife’s presence. She says it’s a romantic mood killer and much prefers me in “Handsome Husband" mode!
Thanks for your response to one of my questions, Petra!
XOXOXO Scarlett
I was 4 or 5 and watched a TV show in which the young star wore a dress for a reason I can’t remember. I must have had thoughts about “dressing" before that because I was mesmerized by the sight of the boy in the dress.
Well I dreamed about it that night. One of the few dreams I’ve had in my life that I can still remember so vividly. This time it was me in the dress. It seemed so right.
Oops ended by mistake.
As soon as I woke up I went to a drawer of my mom’s that I knew had lingerie in it and I pulled out a girdle. As soon as I stepped into the too big girdle…. my mother and grandmother passed by the room.
They both had a good laugh at my expense and I was very embarrassed. What an inauspicious start to my CD career which is still going strong 70 years later. I was a much more sneaky kid after that first experience.
I was really sneaky too and never got caught my anyone in my family!
XOXOXO Scarlett
My first experience was when I was about 13-14. First time I put on my mom’s girdle and stockings I was hooked. Still love girdles 50 years latter.
Sondra
And black lingerie is still my favorite color and will always be my favorite color in that line of femme clothing!
XOXOXO Scarlett
Scarlett- I’m Lara. I just wanted you to know that you have been my model for style and class in the crossdressing experience for ten years or so… Thank you! -LC
You’re more than welcome Lara! I try to capture the attributes of Classy, Sexy, and Cute in each and every photo I take of Scarlett!
XOXOXO Scarlett
You are the best, Scarlett. Keep up the good work… you have a fan!
The things you say to me, Lara, make me feel extra sexy! Thank you for being able to do that to me!
XOXOXO Scarlett
Gorgeous outfit.  
Thank you so very much, Charlotte! This is one of my favorite outfit I creatively put together in just a matter of minutes after those sheer polka tops arrived at my home!
XOXOX Scarlett
Scarlett- You are truly an angel. Your comments to so many of us here on CDH not only are comforting and supportive, but they are also a sign of your own compassionate humanity. I love to read your attentive and kind responses, as I know other members do as well. We take your kindness to heart, and I want you to understand and appreciate the fact that YOU are making a difference in all of our lives… strange as some others might see that… but you, Scarlett, are helping us all in a positive and caring way. Thank you, Lara… Read more »
Completely agree with you Lara! Scarlett is such a special model for all of us girls. We are lucky to connect with her here at CDH.
Totally, and eagerly agree! Â 100%! Â Scarlet you are a model for all of us girls here on CDH! Â Thank you, a thousand times, for your photos, and tender loving responses to all of your sisters! Â Just want to hug you, sooo close!
Stephie
Can’t remember exactly when I started. My opportunities where limited.