What was your first expierence with crossdressing?

As a fetishist, my initiation was a little different than most described so far. My first experience in girls panties was around the first or second grade when my mother ran out of clean underwear for me, she had me wear a pair of my sisters to school. I recall a vague awareness of something stirring within, and that I liked it. But, I don't recall any follow up.

Then, when I was in the 5th or 6th grade, a buddy described how much pleasure he got out of rubbing his mother's panties on "himself". [I am trying to avoid getting banned. :-)] So, I tried it. At some point I figured if it felt this good to just rub, what must it feel like to wear. And, later, if panties were this much fun, what about the rest of the lingery ensemble. And the rest is, as they say, history.

I accept full responsibility. Something just made me try on several of my mom's dresses when I was a teenager. I do remember those zippers in the back being rather tricky. Not like I could ask anyone to zip me up!!! Then I found her dark red lipstick and I was hooked!.....:heehee:

Started at 8 on my own, then on and off till 24 but the last 6 years as often as I can.

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Originally Posted by Alice C

As an only child, I didnt have any sisters to borrow things so i would sneak some time with moms stockings, slips, etc. Was always fascinated by womens clothes and my first big opportunity came wen I was pledging for a college fraternity in 83. All pledges had to show up at a party in drag per the pledgemaster.
I nervously mentioned it to mom and she smiled and shared she thought some of her things were streched out a bit and we would have to go shopping and we were off to her local dress shop. I admit I was embarassed when she advised her SA friend and our neighbor but she was great.
Took me to a dressing room, took measurements and came back with a corset and panties. I blushed deep red and she said lets go and I had the panties on and she was lacing me in to the corset. I swam on the college team and my body was clean shaven . When she put the stockings on, what a sensation. Black dress and accessories followed. Had to undress and stopped with mom for a pair of pumps. On the day of the party, my mom drew me a bath with oils and started to help me dress. She set my hair in rollers and painted my nails in her favorite red color, a first on both counts. I finished dressing and was off to the party. I was shocked because I was the only pledge who went all the way, some guys just put on a dress , amkeup and a cheap wiig. I go a little too much attention , especially from girls who complimented me on the loook and gave a pinch or two.

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Good that sounds like fun! I wish I were that lucky

Self starter here ... was about 5

Self-starter here--way before I knew what sex was!

[SIZE=4]I started at about 4 dressing in my cousin's slips. After that my sisters found out and started dressing me. When I was about 5 to around 10 they kept me as a girl and took me everywhere with them. I even went with them on some of their dates. [/SIZE]
[SIZE=4][/SIZE]
[SIZE=4]So I started it, and they helped me along...[/SIZE]

I believe that it was my own decision as I found women's lingerie and clothes so exciting..........I guess I was 6 or 7 years old and do not think there was anyone else within my family who crossdressed........but do we really know ! :battingeyelashes:

Self starter here

I started on my own. My first clothes were my mother's old clothes and I would do it really discretely and was always terrified my parents would find out. But I guess that made it all the more exciting.

I know this questions probably been asked a million times, but i'm new to the site and it's sort of an interesting topic.

My first time was during the summer right before the seventh grade. i saw a pair of my moms white heels just lying around and the first chance i had i slipped them on. at the time there was a miror leaning against the wall and i could see my feet in the reflection. it was such a thrill! i loved the way the heels felt and looked!

I can't remember exactly how old I was, probably about 8 or 9, I tried on my mum's tights, some shoes and one of my sister's dresses. I only had a very short while, then I had to put them back :sad:

[SIZE="3"]My first experience & memory of crossdressing, I was about 7 or 8years old, I was trying on my Mums green cord skirt & brown suede boots, loved the feeling, Guess who was caught in the act too:D:heehee:[/SIZE]

I can't remember the first time, but one of the first experiences was when my mum left some of her old clothes in my wardrobe because there was space. There was a cute pink dress hanging and I was desperate to try it on. When my parents friends were over I was in my room undisturbed, this was my chance so I tried it on.....The greatest feeling rushed through me, never to be the same again hehe.

http://www.crossdressers.com/forums/...ad.php?t=96753

Happy reading!

I felt my step sisters tights and swimsuit while she was wearing them as children,
then I got into her dresser and got them and tried them on, I liked the feeling and
the rest is history.

I worked in a bar in AZ a few years back and the theme for Halloween was all the male employees dress as woman and the ladies dress as guys. Being an older gent and a bit on the heavy side, one of the gals there helped me out with an old lady getup. A curly blue haired wig and a granny dress, some gaudy clip-on ear rings and support hose. I refused to shave off the mustache, so I looked quite ridicules but we all had a lot of fun. I must admit though it stirred the girl up that was hidden deep inside me. :o

Wow, does this post ever bring back fond memories.......I was a first or second grader and was the only boy of three children. I was an incurable snoop, and was caught by my older sister rummaging through her lingerie drawer. Well, needless to say , she had me in her clutches then!!

She forced me to strip down and don her panties and bra, then her petticoat and dress. Then she added a pair of short white socks and Mary Jane shoes. I was having great fun till she said " OK, you look cute......Lets go downstairs and show Mom and Dad what a Sissy they have for a Son.

I believe it's fair to say my life took off on a completely different tanget at that exact moment!!


Danielle

My first time that I put on a pair of heels (3") was when I was trying on shoes at Payless with my wife. I only had white thick socks on and I couldn't fit into my dress shoes (men's). So my wife gave me those "footy" nylon socks from the store. While I was trying on shoes I saw a pair of black pumps that were size 11. So I tried it on...it was fun. My wife came back and I showed her and she looked around hoping no one was looking...hahaha. Then she asked "did it fit?" and we laughed all the way home.

I am glad this question was asked. I was 8 years old when I discovered my moms nylons. I immediately put them on and started to admire myself in front of the mirror. I was the happiest, even at that young age it had a meaning, needless to say, I never stopped.

First her nylons, then her slips, then her high heels, then her lipstick...and so on and on .....

Not sure how old I was I just know I was young. I would sneak into the laundry room and abscond with some of my Moms stuff to my room. I remember looking in the mirror in the first time think I look goofy. Well of course I did I was a little kid wearing a full size woman's stuff...:heehee:

First experience fully dressed was high school. I went to a Shakespearian theater camp at UMKC. It was a week long and final project was an scene from Midsummer Nights Dream. I "volunteered" to play the part of Hermia. The makeup and outfit were campy but I can remember sitting in the dressing room staring in the mirror in awe at the woman that was staring back. I am surprised I didn't pursue a career in Shakespearian acting :daydreaming:

5 or 6, I would take moms nylons and a pair of pumps out to the back yard, strip down naked put on the hose and shoes and strut around.
Mom used to put lipstick on me when I was little

AS absurd as it may sound? I watned to underatamd girls, amd in my intellect that the best way of doing so was to become one or at least dress like one?

Truth is? I've always been attracted toward feminniity since a young age.

I've tried to deny and kill off my feminine side ~ doing twenty years in the Marine Corps, marrying for twleve years, living with another GG for six and half years ~ its never going to go away.

Remember it well..........No one at the house all day.....wore my mothers underwear and dress............Cannot remember exact date.......however it was the opening day of the 1970 World Cup.........
I was 12

Crumbs I am getting old :eek: :eek:

Yea was in my early teens and home alone after school. I found myself putting on my sisters dress and nylons and walked around the room and mirror studying it all. Felt the chills up my body and knew then this was so wonderful.