I Remember My First Crossdressing Experience Stories of Experiences by most commented stories

I remember my first time as tho it were yesterday,and it happened to be a day which had a couple of firsts...I can't ever remember what made me notice or be fascinated before but at the age of about 9 I remember looking in our airing...

When I was about 7 or so, I tried on my mom's panties and then pantyhose. They were too big, but felt incredible, silky, soft, smooth. I do not know what made me do it, but once I tried, I was hooked, So, I have been crossdressing...

 The new boy in the office is soon whipped into feminine shape
She knew as soon as she saw him that it would be no contest. As office manager she knew a thing or two about how to have her way and one look at the way he came swaggering...

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...

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...

My first time crossdressing came when I was 13. I lived with my mother and her girl friend. My mothers office was having a halloween party costum ball. I was now to old to go trick or treating so they asked if I wanted to go. My mothers...

Every now and then in my childhood, I would slip into my friends house while they were gone, and try on his moms girdles, panties, leotards, etc. Then one day, I was dressing in my favorite girdle, when my friends mom came in the room...

I was twelve, she was sixteen. She was away with my mom for the weekend. I had been really curious about crossdressing for a while, so I took the plunge and went into her room. I remember fishing through her bikini drawer and her...

Although i had been trying my mothers and sisters clothes on secretley since i was about 10 my first real experience was when i was 15 i was at home one afternoon with my older sister of 17 and her friend i was watching tv while they...

I was always interested in women's clothing. I don't know what it was but it just made me wonder what it was like to be a girl. When i was 15 i finally gave into my curiosity and wanted to browse my sisters clothes. I went into my...

It all started , when i was very young i can remember being in a large store and wanting to touch the dresses and lingerie they somehow always attracted me . The silky touch was so nice , Some years passed i was maybe 6 or 7 . My mom...

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...

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...

The first time I crossed dressed I was 14 and it was for a costume party at church. There were 5 of us kids and money was tight. My mom said I would be going as a girl. First she had me put on a pair of her panties then one of her bras...

This is my story of how I got into cross dressing and being with a male.

My best friend Greg and I started to compare bodies when we were around 12. After school on many occasions and at every sleep over we would get naked as soon...

I must have been about 13 , and in the boys brigade . We had end of season display , and I had to dress as a woman for a sketch in the show . I was made up , and dressed in a bra ( stuffed up ) and black tights , and a dress , and a...

Trick or treat night 1978, age 12. My brother and I could not decide what to dress as, so my big sister suggested that we dress as girls ! It was a lot of fun, and we got a lot of funny looks from our friends, but we didnt care. A few...

I started when I was very young also, and then for many years I completely hid my fetish. Now I am comfy with it and express it anytime I can, thanks to a loving and accepting wife =) My first times I thought something was wrong with me...

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...

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...