I Remember My First Crossdressing Experience

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...

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...

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...

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...

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...

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...

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...

This is an account of the first time I went outside dressed in women’s clothes.
I was in my early 20’s and believe it or not, married. My wife was slim and into short skirts and long boots, so there was an abundance of sluttish...

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...

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...

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...

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...

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...

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 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...

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...

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 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 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

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...