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

View all articles by Scarlett398
The following two tabs change content below.


I love the thrill of cross dressing and based on the CDH girls' comments in response to my posted photos, I must be pretty good at exploring the feminine side of myself. I find it sexy, sensual, exciting, challenging, and ever changing. I'm so very blessed now to have as much money as I want to spend on Scarlett and can now, for the very first time in fifteen years, actually purchase dresses, tops, and skirts while shopping with my wife! I never thought that would ever come to fruition! I can now store all of Scarlett's things in our huge dream home when just a short period of time ago, it would all have to be kept in a temperature controlled storage unit. I love Crossdresser Heaven and know it's the classiest and most tasteful cross dressing site on line. All the girls are full of support and encouragement and if folks come to the site with alternative motives which aren't in line with our founder’s rules and regulations, they are quickly deleted from our site. Vanessa Law, our founder, keeps this site classy at all times. She has much help from her Ambassadors, Chat Room Monitors, Photo Monitors, Article Editors, and many more personnel to keep this site classy, encouraging, and supportive.
4.8 6 votes
Article Rating
Inline Feedbacks
View all comments
Lacy Satin
2 years ago

My first experience was at the age of around 8 or 9. My younger sister asked me if I wanted to play dress up with her. I was very excited over the thought of playing dress up with her because it was something I have wanted to do for a long time before that. I don’t have much memory of those early desires but I remember going into my sister’s room and looking at all her pretty dresses and wanting to put one on but they were just too small for me. How we were going to play dress up… Read more »

Baily Marie Lovejoy
Active Member
4 months ago

Just getting to read this dear. What a great story. The first time I dressed I had found my little sisters nightgown. I was 6 or 7. I fell in love with the feeling and the notion of being a girl. From that point on it’s been I battle inside me to want and realize who I am. While growing older it was admittedly, at times, a sexual experience. I think mostly it was just the inner desire to be feminine. To be female. There was no thought, no possible way to do this back then so I thought. I… Read more »

Baily Marie Lovejoy
Active Member
4 months ago
Reply to  Scarlett398

I know what you mean girl. I know what you mean. Wish I could get back all the lost time and some of those outfits were just adorable. And me heels. Oh god girl, my heels, gone. lol. Makeup kits. Everything purged. 😱
But hey, here we are now. This wonderful site that we can meet and talk to other girls I wouldn’t trade this girlfriend. Not for any of those purged items

Hugs Scarlett 🤗 you’re a doll and a good friend

Baily 🎀💁‍♀️🎀

Tyra Lawn
4 months ago

When I was 6, my older sister was having a sleepover at our house with about five of her friends.  They all knew me and I even had the biggest crush on one of them because she was the prettiest of them all.  Anyway, they were playing dress up and each had brought something to dress up in and then my sister decided it was time to add me to the mix.  So they each had input and the result was me standing there dressed as a girl.  At first, I protested and told them I didn’t want to dress… Read more »

Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?