I Remember My First Crossdressing Experience Stories of Experiences (Page 8)

Do you remember that first time you put your first high heels on, and how it made you feel? I will never forget that first time going out as a young girl. Like most of us I played around with my mom's shoes and clothes, nothing really...

Growing up I had two older sisters who were dancers, They were in lots of shows and had lots of girly costumes that ended up in the basement for them to play dress up.

Little do they know, I wore all of their costumes a lot more than...

When I was in high school the cheerleaders were always trying to get some guys to join the squad to help them with stunts. I was dating one of the JV cheerleaders at the time and she convinced me to join up. I got to know most of the...

The first time I crossdressed I figure can be best described in three way: the first time I chose to crossdress, the first time I crossdressed with a friend, and the first time I crossdressed in a relationship.
The first time I chose to...

Much like many of you I started perusing the Sears, JCPenney, and Montgomery Ward catalogs. When you're just coming into puberty its a big deal to see women in their underwear. Eventually I started to wonder what it would feel like to...

Ah the first time was it so long ago? but i guess thats why it was the fisrt time
mine was when i was 20 it was my fist time going full out as girly as girly can get !!
it was so amazing i fellt so beautiful and felt so true and free...

I enjoy going out with lingerie under loose fitting clothes while I shop for ladies things, I've even started wearing women's clothes out, though only pants and lounge wear, Danskin exercise bottoms mostly, I've gotten a few looks...

My first time dressing myself up came when i was around age 12. My sister used to ice sKate but had recently quit, and all her ice skating dresses were in a bag in the corner of my moms office. Everyone in my house was gone and the...

I was 9 and it was not long after my sister first introduced me to dressing up. My mother, a growing supporter of my budding feminine relationship with my sister, told us she just bought us matching devil costumes. I suppose they were...

From my earliest memories I remember liking girly things. I had an older sister and when I was very young I was always more interested in playing with dolls and cooking sets than other toys. I was always more interested in hanging with...

The first time that I recall having an interest in crossdressing was when I was about 10 years old. It was Halloween time and there was a costume parade at school. For the life of me, I cannot recall what I wore, but there is one...

My friend was desperate to end some teasing he had been subject to concerning him not being attractive to girls in anyway,
As I was also in the same situation ,I wanted to help him anyway I could.
His request was not unreasonable and...

I do not know why,how,explain,what gave me the idea,,all as i remember,is my mother used to leave me home alone,babysitting my young sisters,2yrs,4yrs,5yrs old,i was made do housework,washing ironing,cleaning etc,i was 9/10yrs old,,i...

I do not know why,how,explain,what gave me the idea,,all as i remember,is my mother used to leave me home alone,babysitting my young sisters,2yrs,4yrs,5yrs old,i was made do housework,washing ironing,cleaning etc,i was 9/10yrs old,,i...

My first cross dressing experience happened in college at the age of ninteen. I was a naive, horny sophomore who thought about girls every waking hour.
In the dorm, it was natural to talk about sex and to read Playboy. The pictures were...

this groups avatar must have a story associated with it some where..I would love to read it..

Bri

During the first 15 years of our marriage every once in while when the wife and kids were gone for a while I would do dress up again. That was about twice a year. Not near enough of me. Then I started having pains in my knees from...

Ever since my mom cross dressed me for the party I wanted to wear women's clothes again. While mom was at work and I was home alone (which wasn't often) I would go into my mom room and strip. I would put on panty hose with no underwear...

My first time cross dressing I was 10 at the time and I was spending the night at my grandma's. She dressed me up in a sexy nightgown, panties, pantyhose, makeup and a wig. I have been hooked ever since!

My first chance at going out crossdressed was when I was around 22 yrs old. I decided to go out and buy some sexy lingerie at Frederick's of Hollywood. I bought myself a 1/4 cup lacy bra with matching panties and garter belt. I...