My First Time And I Have Not Stopped

By: matty69
Written on July 7th, 2012

I must of been 9 or 10 and was playing outside in the yard. I was a normal boy at elementary school who enjoyed baseball and generally throwing balls about. Then, one day, I had this sudden urge to wear girls clothes. To say that it came from left field is an understatement to any ball park I know. What was more surprising it that I decided to do it immediately.

I rushed upstairs to my sisters room and went straight for their underwear drawer. I pulled out a pair of semi large pink briefs that I had seen before in some subliminal moment and took them back to my room and hid them. Next, I planned to find a dress to complete this sudden urge that was taking over me. I cannot tell you how strong, sensuous, thrilling and exciting it was. Luckily for me, my sisters overspill closet was in a guest room that was empty.

I picked out a short navy blue pleated skirt and rushed back to my room. Then the moment came as I put the pink panties on an zipped up the skirt. I was so happy and liberated.

My crossdressing has been a part of me since then. Like other members, I used to go through used clothes sacks in the garage picking out what clothes I could wear.

Now I use most occasions at home to crossdress and the whole online shopping world has made this easier to achieve. I love wearing skirts and pantyhose and favour the "office look". I go for plain navy and black straight skirts with dark, 100 denier pantyhose to match. I would not change the way I have become and the thrill of the experience is so difficult to describe. Its part of me and I am part of it. I hope some of you will share your experiences if they are similar to this.
matty69 matty69
41-45, M
4 Responses Jul 7, 2012

A super account of what its like to be a young crossdresser !

Wonderful experience Matt. I think we all have had a FIRST time. Mine was when I was eight years old. Like other boys of that age, I was curious about almost all things feminine/girlish. At that ttime I didn't understand why, just that whenever I saw a pair of panties in store windows, or photo's of them in a magazine, I'd sit and look at the photo's for a good amount of time. My first experience with actually touching panties was when I finally got enough courage to look in my mother's lingerie drawer..looking turned to touching, and finally wearing a pair of her panties. I remember I was so scared of getting caught I wasn't too selective of which pair I took. They happened to be a pair of white nylon full brief panties. I later took time to look at the little tag sown inside, and it said Vanity Fair, size 6. That was later in age, probably around 10 or 11 years old. That first time, I took the panties into the bathroom, slipped my jeans and shorts off, then with glances to the rear of me making sure I was alone, even though I had locked the door, I was terrified of being caught, and knew that I was doing something (in my mind) very wrong, and naughty. I still remember the feel of the nylon panties being pulled up my legs..the leg elastics tight agains my upper thighs, and finally encasing my little penis. All I could do was stand in front of the mirror and look at myself. From that day onward, it was a matter of adding something different whenever I dressed...a bra, a slip, nightgowns, girdles, stockings, mostly during my younger years...when I reached the age of 13 I began trying on skirts, blouses, anything I could find in either my mothers room, or my older sisters. I am now 20 years old, attend college, and share an apartment with another boy who after being around him, and testing him with questions about did he ever do this or that, in regards to wearing female clothing, it came about that he did, like me when he was younger...and he still enjoys the thrill. Sometimes we wait until one of us is alone before dressinng, and there have been a few times when we have dressed together. It is fun to talk about clothes, what looks good, favorite outfits we are not gay..just enjoy dressing!!

I will never TRULY understand why we like women's clothes so much, but we do.<br />
Boy, doesn't it feel great to just get those damned man jeans off, and put something<br />
"more comfortable." Me? I love sleeping in my nightgown, no pajamas or tee and shorts. Nightgown, the ultimate way to rest.

A nice way to start crossdressing