When did you first crossdress?

[Lacey New]

When did I first crossdress? Hmm good question. Maybe I'll answer like Bill Clinton - depends on what your definition of crossdressing is. Definitely in my early teen years, I developed a strong panty fetish and I borrowed my sister's and mother's nylon briefs whenever I could. I may have even put on a bra from time to time but all of these experiences were very quick with one goal in mind. I do remember though being fascinated with the small advertisements that were in the back pages of Penthouse and Hustler for a place called Michael Salem's TV boutique. So, curiosity was definitely there.

Then in college, a girlfriend left a pair of panties and pantyhose and I did not bother to return them until I had tried on both. I remember the feel of the pantyhose and it was - well, you all know - great. After that, my opportunities were few and it was not until I got out of college and I was living in an apartment on my own that I first bought my own lingerie. First just panties, then a bra and soon after, the whole range of lingerie inclusing garter belt, stockings, slips, camis, etc. I think at that point i had probably "crossed over" Even though I have purged many times since due to moves, marriage, kids, etc, I keep coming back.

[Denise1951]

My story is typical. I was 5 or 6. Started with my mothers slips and went from there. All my childhood, all I heard from her was. "I wanted a Girl." "I told the doctor to take you back, I wanted a girl." and statements like that. I was going thru home movies a few years ago, and found movies of me dressed up for Halloween. I don't remember it. When I got into high school, I decided to go buy my own cloths. Once I got over the fear of taking them to the checkout, I ended up with a nice collection. It was the mid sixties, and I discovered the "bra slip." I was hooked forever.

[kristinacd55]

My sister's full slip hanging and drying by the tub, when i was taking a bath. I was 6 or 7 and loved it! hook line and sinker

[NicoleScott]

I started around age 6 by putting on lipstick behind a locked bathroom door. It wasn't clothes, but I think that qualifies as a crossdresser activity. I didn't start putting on my sister's clothes until around age 10. Lucky for me, my sister and I were the same size (shoes included) throughout several teen years.

[Roberta_C]

At about age 13 or so I tried on a girls hockey skirt to see how I would look in it. Loved it! And that's where it started for me.

[Kari B]

Tried on my mums pantyhose when I was about 12 I think. Just to see what it was like. Took them straight off, but the seed was sewn. Always feel sexy and comfortable when wearing.

[Tammy Nowakowski]

Hmmmm, I think whan i can remember is when my got sick i was about 14 i tryed on one of her bras and a pair of panties both wear to big for me

then one day i went of over to my girl friends house she left her room for few mins i grab a pair of panties and a one her bras they fit just right

[michellecd9999]

I was told my baby sitter used to dress me up when I was under 1 yr old. But the first time I did it was around 12-13. Put on a nightgown.. one of those layered things of nylon and tricot. This would have been around 1969. I loved the feeling. Then moved on to slips, hose, pantyhose, panties, dresses, shoes, etc.
Did not dress fully in wig, makeup until I was in my 40's.

[Rachael Jones]

Must have been ten or eleven or so. Just vague memories of wondering what it felt like to wear tights, and the feeling of legs being free under a skirt. Fantastic, so it's carried on and off over the years.

[Danielle_cder]

Not soon enough... bout 5-6 aunts panty hose got me

[CynthiaD]

When I was three I begged my mother to wear nail polish. She painted my nails and I was in heaven. All the other kids in the neighborhood made fun of me, but I didn't care. A year or two later I begged my mother for a ribbon to wear in my hair. That was a bit disappointing, because my hair was too short, and it kept falling out. I don't remember all of the steps, but by the time I was in high school I was dressing fully, and thought of it as "just something I did."

Despite my early start, it took a long time for me to be really OK with it. I grew up in the 50s and the world was a very different place back then.

[MysticLady]

I remember trying a pair of mom's pantyhose that were hanging on the shower door left to dry and I was hooked.

[missmars]

nine . I tried moms bra.

[BillieJoEllen]

I had as a child been dressed in girl's clothes numerous times. I had always considered myself a girl/woman. I don't know if others saw that in me. I was never drawn to female clothes as a child. If I found myself in girl's clothes in any way shape or form I hardly gave it a second thought. Sometime around when I was nine or ten I started realizing that there really was a difference between boys and girls and I started coming to terms with the fact that we were 'different'. At about that time I got my clothes dirty while playing on my aunt's farm. She dressed me in my girl cousin's clothes. I was deeply embarrassed and humiliated. I continued after that to allow my mother to use me as a dress model for dresses she was making for a girl cousin although I was very sheepish about it. My mother encouraged me to use a costume for Halloween that she made for my older sister. That costume lead to conversations with girls in my fifth grade class and they encouraged me to 'experiment' with different girl's clothes. Up until then I could've stopped CDing and never look back although I still had very deep feelings of being a girl. When I was encouraged to try a certain combination of girl's clothes I was 'hooked' and I knew there would be no turning back. Although I don't think what I had experienced before was really CDing I think at that point is when I really became a CDer.

[Aylineira]

Definitely around 5 years old. I put on my mom's red heels and pranced around in them.

[Christinedreamer]

I am currently visiting my older sister and I asked her what her recollections about my early dressing were. She said the first she remembered was when I was about four years old and discovered my oldest sister's new pink babydoll PJs. This was around 1957. She tells me I would get them out of the drawer and wear them around and loved to take a nap in them. Mom was not too keen on this but didn't throw a fit.
Then on Christmas, my grandmother gifted both my sisters with new, really cute babydoll sets. My older sister got a lime green double layer set with double layer bubble panties and my oldest sister got a fire engine red set. My grandmother though had not looked carefully at the red set. They were one layer and quite sheer. Obviously my sister could not wear them around the house and so she buried them in her dresser drawer under the more traditional stuff. I discovered them and as they fit me perfectly, I snuck them into MY dresser. As with most every one else here, I was hooked on the feel of the material. My older sister was too shy to wear hers but did not hide them. One day she found me wearing the red set and teased me about it. She went to her room and got hers and said "here you can wear these too. I don't want them".
She goaded me into putting them on over the red set and I did. The thrill was electric!
Just then mom came in and was seriously pissed. My sister said she found me wearing them. Mom believed her and said I was going to wear them until dad got home and saw me in them.
When dad got home I was marched out for him to see. He just said " I see you like your sister's clothes. Want some of your own?" According to my sister, I just stood there. Mom said maybe I should wear them until I got tired of them and dad agreed. I do not remember much in the way of details now, but My sister tells me I wore them every day after school, the entire weekend, and slept in them for a month. Mom made me stay in bed naked while she washed them and then I had to get dressed in them again. Whenever I was with my family I was dressed in them. Pat says she thinks this went on for at least a full month, maybe longer. After that I found mom 's nylon nightgowns and really got started . They only took one picture of me dressed in them and I was sitting on the couch next to mom. We are looking for that picture now.

[CassandraSmith]

Three years old. Slipped into mom's girdle and jumped into bed. When she saw, she told me to take it off and put it back. It felt soooooo right though; I knew I was different then.

[becky77]

I think I was too young to remember, I have a vague memory of trying on my mums boots and could only have been about 5 maybe older? It feels like it has always been there so I have no real definitive start point?

[danielleinbr]

When I really think about it, I guess about 5 or 6 my mom had some really cool high heeled red boots. That is the first thing I remember. It started progressing slowly in my teens then went into overdrive in college.
Danielle

[ArleneRaquel]

Between the ages of 6 and 8, I don't remember what I wore the first time, but in one of the first I wore my mothers gloves, high heels, and jewelry. I have loved woman's fshion for almost 60 years.

[AlexisRaeMoon]

Does just sticking socks in your shirt count? Then 5 years old. But actual female articles? Probably 13. That's when I started being left home alone, and discovered mom's shoes fit. It was downhill from there!

[alexbowral]

At the age of 17 yrs I tried on a bra and panties, I have dabbled on and of for very many years, I have only been serious
over the last 12yrs. it came about after my wife passed away and I had to clear her cloths she was about my size so I tried some on , and from then on I nave become rather obsessed and now buy cloths that I rearly suit me.Mature maybe but thats fine.

[Tara D. Rose]

My earliest recollections are from around 3 or 4 years old. Though I had to hide it,it was so natural for me.

[Xandra]

Thanks to all for responding - I've really enjoyed reading everyone's recollections. It's curious that what started at an early age just doesn't go away.

[SarahMarie42]

When I was three or four years old, I used to beg my mother to buy me dancers' dresses and tights and shoes. I didn't quite get the shoes or too many dresses, but I'd occasionally get the tights and a skirt or something -- I would become implacable if I couldn't have them. Lol.