I Remember My First Crossdressing Experience Stories of Experiences

April, 1964--I was about 12 1/2, in 7th grade, and in love with Kathleen, a red-haired girl who was a dedicated student of ballet. It was Friday afternoon, the day before her recital, when we walked toward my Aunt Jeanette's home...

I was about 10 years old and at my grandparents house. Both of them gone to work. I was really horny and looking at my grandmas panties. It made me feel right so I tried them on and then I tried on one I her bras the. I went to her...

Happy mother's day, to all moms of the world and, to the boys they wanted to be moms. All my family knows of Fernanda, even my daughter and my son.

One day I dressed nicely for dinner with my mother. When leaving the house, I received...

I was about 9 years old. One day my younger sister asked me if I wanted to play dress-up with her. I didn't hesitate for a minute before saying "YES!"
I don't remember all the clothes we dressed up in. What I do remember is after...

Well that is a story. My wife was at work so after she left I got dressed up for a morning of shopping as a woman. I put on a nice pair of women's black slacks, bra, white blouse, cami, pantyhose, panties and panty girdle that had...

Finally go to department of my friend Rina, I left my stuff on the bed I undressed and took a bath. Shave, it was easy because At that age the beard is scarce (I tend to be hairless). So do not shave my legs and armpits. Upon leaving...

My first time cross dressing was when I was 12/13, I was just getting out of the bath and on the floor was my sisters clothes. A skimpy black thong a tight fitting pair of jeans and a black low cut top and a black lacy bra. I looked and...

My first crossdressing experience consisted of my older sister playing dress up with me as her doll. I was about 5 years old; she would have been 8. She put me in one of her old dresses, with white anklets and black patent-leather shoes...

I'm a guy who likes to wear women's clothes, I like to wear my sister's clothes right now I'm wearing a dress stockings and shoes and a pink bra I started this I was 11 years old when I was in my room and suddenly saw a heels of my...

I was in the back yard my mom had clothes on the clothes line. I wanted to see what it was like to wear a dress. so I striped in the back yard and put one of my moms dress on it was scary and very nice at the same time

I was around 12 and of course it was my moms bra. I liked the feel but it was too small. I wanted to have big breast. My next bra was my aunts ( god i loved her big tits ) . I got to stay with my Aunt and Uncle and cousins. The first...

My first crossdressing experience was just out of curiosity, i had never felt the urge or want to dress in women's clothes or underwear. I just got out of the shower and saw my mothers bra on the cupboard, I thought why not. As soon as...

well i was in my 20 and my gf and I went away on a short vacation. we got to the motel and she said there was a surprise for me in the suit case and soon as I showered up we would play. so out i came and there was lace pink panties...

I had to travel a long distant to see my doctor and several times I thought I would love to do it as a women. I had been told by many not to do it especially if I got into trouble driving. Well I thought about it for a long time and on...

When i was little i was forced by my mother to go to a girl in my classes house till she got home from work. while i was their i was forced by her and my sister into a closet till i put on makeup nail polish a dress and her bra and...

The big day was scheduled for Friday December 18. That day I got up at 10 in the morning, because I fell asleep at 4PM, because I was very nervous in the morning due to excitement about what would happen this Friday night.
My mom told...

So as you might know I am a crossdresser. I love to dress up and let that sissy out. Ive only ever told one person and we don't talk anymore. It's a complete secret other than her knowing.
So I started out with very few items of...

Im just home from church. I have jeans on. Under the jeans I have green bikini cut type panties on. I have a collard blue polo shirt on with a white training bra with a cute red rose in the middle of it. This is the first time i went...

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...

the first time i CD i was 11, it was a saturday, my sis was out with her friend for the day, my mom was fast asleep after workin graveyard, after takin a shower i walked into my sisters room in a with my spare clothesl, i had been in...