I Remember My First Crossdressing Experience Stories of Experiences (Page 4)

Well as it was only a couple of weeks ago and such an unusual thing for me to do it's a bit hard not to remember.
Nothing too exciting and I suppose the first thing any man who wants to experiment with simple cross-dressing would go for...

Happened by accident.The family shared 1 bathroom in the house we lived I was about 10 years old and wanted to take a bath before bed time.My mother accidently left a pair ot black panties and bra on the floor.Half way through the...

First of all hello to all my dear frnds,i hope u will give me ur ideas,help n support to me,as I m a matured person of age 21,but this all started at the age of15 when my mom was busy sleeping n my god promise I m not lying I was...

So today was the first timemy mom saw me crossdressed. Today when I got home I ran into her room and put on a black laced thong (witch I have on now), black pantyhoes (think enough could be leggings to), a black cowl neck sweater ( my...

As I recall I was 12. I think I watched some T.V. show where the women was trying to be famous and wore a bodystocking. This I can remember. I then started to become at the same time interested in the tights of the girls at school...

I think I really should have posted all these stories about my teenage years in a "forced crossdressing" forum, as they're not exactly gong to be a lot of fun to those of you who enjoy wearing women's clothes and might be hoping to read...

Here's a follow up to my first story - it's about another set of firsts.
It was the first day back at school after the summer break and there I was, an adolescent boy just short of my 14th birthday,looking at myself in the mirror after...

My first time was when i tried on my moms bathing suit I was about 9 years old. It was a one piece that was black and blue. It was on the back of the bathroom door while we were on vacation and I just had to give it a try to see how it...

Growing up with a curiosity about crossdressing led me to trying on various items of clothing as the opportunities presented themselves--a skirt here, shoes there, etc. The tipping point (and what i think of as my first real experience...

Some human tendencies may seem odd, or inappropriate, or even socially unacceptable. However I believe that these tendencies may be imbued by nature from ancient times.

Going back thousands, and thousands of years to neolithic times...

I was about 14 years old and when I got home from school I decided I had to try on some of my Mother's clothes as she was busy in the garden and would be out of the house for at least an hour.So I stripped off quickly and the first...

The day was a blur but, with the benefit of hindsight, was one that several people made such an effort for me to realise my dream. Tia had  produced a lavish creation that defies description. Mother was beside herself with joy...

I can remember it like it was yesterday, we were about 7 or 8 yrs old and a couple of friends and I were playing street hockey in the school yard.
We had been playing for about an hour when I noticed Lori sitting on the step watching us...

Tia insisted that mothers permission be obtained. Indeed, we would need her help.

That night, at home, I struggled to find the moment. Helping with dinner, eating and clearing away, I just couldn't spit it out. Finally, in...

I grew up different
my older sis didnt want a yunger brother so around 4 or 5 she started dressing me
Mom thought it was cute and went along with it
They would take me shopping,to the restaurant,just about anywhere
Even to school in...

All I really remember is: I was on my old laptop one night toward the begging of 7th grade, going to watch porn (of course). But than I saw a category that i thought "Aw, what the hell" Shemales. So than I wondered "what would it be...

That is an interesting question. Thinking back I remember when I was around 10 sneaking into my mom's closet and slipping on a pair of her black high heel pumps. I had never felt anything so incredible in my life. They gave me tingles...

I am very awere thag steeling is iligal but I wanted some your oppinions. I am staying the night over my friends house and I walked into his older and little sisters room and I saw a thong just sitting right there on the floor and im so...

So I finally talked to my mom about crossdressing.I was sitting in my room and I really wanted to put on some of her clothes sooo bad. So I sent her a text asking "Can I put on some if your clothes? Im still crossdressing the only...

I guess like many men my first experience was at Halloween. It was my mother's idea to dress me up like a little girl. I was about 10 I think. She had borrowed some clothes from the daughter of our neighbor. She was a year younger than...