Welcome to Crossdresser Heaven, a safe and welcoming place for everyone in the crossdresser community.
Join Crossdresser Heaven today to participate in the forums.
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
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 a dress to wear, and we spent many happy hours making up stories to act out. I can't recall any details, except that I was comfortable in the role, and not at all shy about the girls and their mom seeing me in a dress. The fun ended when I moved away, and my next chance to Dress didn't happen until I was in high school and came across a discarded sun dress in a storage room.
Bettylou
