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.

Crossdresser Superstore

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

 

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Bettylou Cox
Duchess
Active Member
25 days ago

Hi Scarlett, My first crossdressing experience was much less dramatic than yours (and much further in the past), but still memorable. With no mom nor any female relatives, my initiation into CD fell to Norma and Naomi, twin girls and my favorite playmates. I was in 4th grade, so I would have been 10, and the game we played was “Tarzan, Jane and Boy” (Johnny Weissmuller being a huge star with kids at the time). And did I get to be Tarzan? Nope, the girls re-wrote the script; Boy became Girl, and that’s who I became. The girls gave me… Read more »

Peggy Sue Williams
Duchess
Noble Member
25 days ago

Scarlett, So good to see your photos again and now see an article written by you! I can’t say as I had an actual “coming out,” so to speak, or a very first CD experience. Looking way back in my memory, it seems that I always was doing some sort of CD thing, and my parents were aware of it. Practicing walking in heels, applying make up, trying on dresses, etc. I split my elementary grade school years between spending time with male playmates, doing boy things and also spending time with girls, doing girl things. I learned many basic… Read more »

Mona
Duchess
Trusted Member
23 days ago

Scarlett, Glad to see you are back from the dark place you were stuck in. Rest assured we were all pulling for you. I think it’s courageous of you to share these rather intimate details of how it all started for you. While the details might differ, the basic plot line is the same for a high percentage of us CDs. And we still don’t have an answer to the eternal question: what is that “urge” that started it all? Where does it come from? We know that the vast majority of other adolescent boys in your situation would be… Read more »

Amy Myers
Baroness
Noble Member
23 days ago

Scarlett, thank you for sharing that amazing experience with us. Mine also wasn’t quite as dramatic, though similar. It was somewhere around when I was 12 or 13, and the key there is that was when my parents would leave me at home alone for while they went out. I found some of my Mom’s undies, a girdle, bra, and a corset like item. I just loved dressing up, and it became the thing I’d do when I had the house to myself for long enough. I was caught twice, as I remember it. Once I forgot to put on… Read more »

Lucinda Hawkns
Active Member
22 days ago

lovely story. I started with a pair of tights in a school play and was hooked from there on. but was on and off . then came back stronger and never stopped. I love pitting on nice fitting panties, Cupid panties, lacy bra and a sexy dress, then make up and perfume and ear rings, then heels. i dress from head to toe when I have the chance to and love it so much wish I could stay dressed up a a female. real woman do not dress like real woman now days its pants and a over sized shirt.… Read more »

Dorothy Brinson
Member
21 days ago

Hello Scarlett, My first time cross dressing. I was maybe 4 yrs old. I remember wanting to wear one of my sisters dresses. I put her dress on and hid in the closet. When I was 7 or 8 I started playing dress up with my sister and her friends. The girls always put moms cloths on over there’s. I always took mine off and put on moms cloths. Oh the feeling of those silky panties against my skin. I was hooked. As a teenager. I would dress up in my room with my moms lingerie. My mom would get… Read more »

Tammi
21 days ago

Hi Scarlett

This subject sent me to the way back machine. When I was 9 I found a pair of my cousins panties she left after an overnight stay. Soft nylon baby blue, I couldn’t resist trying them on and was hooked. From there I started wearing those panties, moms girdle and dress.
I have never been caught. I continue to dress when I can close to 50yrs later!

Tammi

T.J. Byron
Duchess
Trusted Member
21 days ago

MS.”S” ….You are truly amazing( a word a clerk at Walmart used to describe my look last week!), we have all told you how truly beautiful you are.
We love seeing pics of you, Girlfriend!
My 1st time, I was about 5-6 y.o. and used bedding and towels to create long hair, and feminine garments to run down the Hall Way. From then to now…A closet full of female clothes and shoes! Dressing, going out weekly.
Love to all…Dr.T.J.

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Frederica Woodbridge
21 days ago

My cross dressing urge has been with me forever. It started with me wearing my mother’s nylons when was 12, then adding her boots and bras. I’d supplement that with removing nylons and panties from washing lines or sneaking in someone’s house and stealing underwear. My wife died from cancer 8 years ago (I wore her nylons when she wasn’t watching) and then I descended into rampant cross dressing at home. I met a woman who actively encouraged it, and we’d go out with me en femme together for dinner……..great fun, but never completely relaxing if you’re 6 feet tall.… Read more »

Frederica Woodbridge
21 days ago
Reply to  Scarlett398

I realised I didn’t answer the question about getting caught. The answer is ‘not directly’ but when I was about 16 my mother discovered my collection of stolen underwear and nylons. My response to “where did this come from’? was staggeringly feeble, but no further questioning. Couldn’t believe it. Since then, underdressing with the young lady and getting caught is brilliant fun.

Jane MacLeod
20 days ago

Hi Scarlet. First experience I recall is wearing tights at a young age. Most have been 4 or 5 but honestly can’t recall when or why I wore them but remember wearing them often but not openly. Remember when was about 12 or 13 sitting in a pair of tights and going to try a dress on with heels. Was very aroused by this and certainly was a big part of my dressing and still is to a degree. Started getting more adventurous putting on bra and panties. Trying make up etc. Remember first time got to wear stocking and… Read more »

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