When was your first time dressing?

[Cithmore]

I was 7 and my 13 year old sister and cousin were baby sitting me and trying on her underwear in her room, I was watching them so they made me take off my clothes and they took turns dressing me in bras and panties and laughing. After that I would take my sister's panties and wear them all the time, she did not mind as long as I did not wear her new ones.

[Chrissi]

I was probably 7 or 8, my next door neighbors only daughter was in high school. She would dress me in outfits that she had when she was younger.

I loved it and so did she.

[Jennifer T]

I was about 11 when my mother would let me wear her underwear and lingerie. It was a great time!!

[tami_cd]

i was 12 when i got caught trying on leotards with my sisters skirt . couldnt say that was first time tho but its the time i remember most =)

[Miley]

I was so young it is hard to remember. My family would always go to a friends house and I was best friends with their daughter who was the same age as me. I would try on her skirts and play with her barbies. Also about that time my mum kept some of her clothes in my cubboard so I remember when I was very young wearing a pink dress of hers. I remember on time I was wearing my frineds skirt in her room and my parents opened the door. I dashed to hide behind the bed and quickly took of the skirt and jumped out pretending to surprise them.....that was the beginning of many close calls that would come in the future...hehe lol

[Michaela42]

My female cousins were babysitting for me. I was around 7 or 8 and after busting me trying on their shoes they had left by the door they took me upstairs and dressed me up. They were all well into their teens so nothing fit too well :sad: but none of them mentioned the incident to either their or my parents :)

[tami_cd]

ya close calls ... needless to say i was more cautious after that.

[Bobbi McCarthy]

I was nine when I started to secretly wear my sister's panties. She was a year younger but nearly the same size in everything. I would sneak on a pair of her panties whenever I found the opportunity. Her underwear was mostly cotton but a few were silky nylon and especially girly and well, in a word – wonderful.
One day, my mother caught me wearing them and questioned me adding a stern rebuke and threatened to tell my father. I was of course mortified and frightened sufficiently that I did not wear them again for months. But in time her threat wore thin, but the memory of those panties remained. I guess she knew, because one day I found my underwear drawer stacked with newly purchased Vanity Fair panties in my size in a variety of colors. I ran to her and gave her a big kiss without providing a word of explanation. She knew, then smiled.
That event signaled for me an open door to be able to talk about my desire to dress. Mom was sympathetic to a limit, and continued to add to my secret wardrobe. My father was at sea in the navy for much of my life and he was not a partner to or ever knew of this secret. It was a mutual conspiracy that included my sister. My mother was supportive, enough so that she also introduced me to shopping enfemme. I was ten.

[tammygirl79]

I was probably 12 or 13 years old. My parents would go out every Friday & Saturday night. One night they left, and I went into my moms closet and tried on her bras & panties. I just loved the way the silky/satiny material of the bras & panties felt on my skin. I was hooked from there on out. Of course after a few weeks, that lead to me eventually trying on her dresses as well. :)

[GiMae]

Compared to most of what I've read here, I'm a very late starter. I don't remember any serious cross-dressing (some horseplay with other teenage guy friends when too much alcohol was involved) in my past until just a couple of years ago when I started wearing pantyhose as lightweight thermal underwear while motorcycling.

That would have been around age 55, a mere two years ago.

Thanks,
GiMae

[t-girlxsophie]

Wore my Mothers clothes at 10,remember first time I was found out,was staying at my grans,and wearing my Aunts yellow maxi-dress pink cardi and hose.Think my style now reflects what I wore back then

[Dana]

Since a vey young age (four or five) I've always have been attracted to women, femininity and such.

When I entered puberity my sister (who I later learned was my half-sister) moved in with my father and I.

My ratonallity in trying on her red nylon panties with a zipper up the front? Was in trying to understnad girls and women.

That started it!

I've attempted to deny it!

Resist it!

Deny it!

Thought marriage to a GG would cure me of it? It didn't!

Thought enlisting into the Marines and doing twenty years in the Marine Corps would cure it?

It didn't.

Truth be told? Now that I'm retired from the Corps?

The children are grown and on own their on?

I would love to find a GG and be the "wife" in the relationship.

[Pattie O]

Very first time was around 4 but it was only mum's pantyhose and a hair clip and some lipstick.The first real dressing I did was early teens 13 yo and I would love dressing as fully as possible at home whilst nobody home.I loved full corsettes and pantie girdles and satin blouses ,mid length woolen skirts and heels.I would do make up and use hairspray (miss my hair) and loved to then dance to some music often George Benson or Nicollette Larson.Dreamy

[CourtneyBleu]

I started when I was 4! Too young..?

[Colo Deb]

It was so long ago that I don't remember many details, I was about 7 years old. My sister and brother played house--there was a collection of old dresses in the old house on the farm. They were really too big to fit any of us, but we played in them.

As a teenager, my sister and I found a couple of mom's old swimsuits in her (sister's) closet. We tried those on -- loved it! I also got into some of mom's clothes when I was home alone, but that only happened a couple of times.

Fast forward about 25 years--I ran across a cross-dressing forum while at work. I was fascinated by the stories, and soon began to build my wardrobe. That was 15 years ago.

Deb

[BRANDYJ]

I was 10-11. I found a box of clothes in the vacant apartment above the garage of the house my mother was renting. I tried on the clothes and got very excited and at the smae time was so nervous I was shaking. This was after my first contact with my mother's ful white slip that was hanging on a hook on the back of the bathroom door. I did not put it on, but let's say it caused my first ever orgasm. That too frightened me to no end since I had no clue as to why the very strong feelings and eruption was something I had no clue about.
Oddly enough, I never wore anything of my mothers.(or younger sisters) I think I must have felt that her clothes were off limits and it would be an invasion of their personal things if I used them for what started out as a sexual thrill and grew to be so much more then that later on.

[victoriamwilliams1]

5 years old and it started because I had to wear my cousins dress for it to be hemmed! and it happened a few times and I liked the dresses! :)

[Cait]

I first started playing around in heels, make-up and jewellery around about 4-6ish. At around the same age, my mum would get me to try on girls fancy dress costumes she was making. By around 7-8 I was dressing up in my sisters clothes (and pretty much any female clothes I could lay my hands on) on a regular basis -dresses, skirts, tops, shoes, the works. I think its fair to say that I started fairly early :)

[suchacutie]

Age 55, for my wife using some of her clothes and some I purchased. Certainly a life-changing moment! Within 2 days Tina was named, had her own e-mail address, and was trying on dresses!

tina

[bionca]

I must have been about 9. Don't know how it started, but was looking through mom's drawers and started taking interest in her panties. I remember finding white stockings and garters. I waited until I knew I would have enough time to try them on, these new, delicate items. I remember vividly taking my time to learn how to put them on and do them up. Such a sweet and innocent memory for me!

[Joankristy]

Your so lucky to have had a mother that would suport you.

[kimdl93]

I've answered this a few times since joining the group - but for the newbies- I first wore my older sister's slip when I was maybe 5-6. I started wearing panty hose and panties around the age of 16. Then another lull, till I was married and my (now x) asked me to put on her panties, bra and pantyhose during a lovemaking session. I underdressed for years, through that marriage and into this one. I started dressing more completely when I remarried, with my wife's support, and now dress nearly 24/7 (when the grown kids are away)

[Kate Simmons]

Probably when I was around 5 and put a dish towel around my waist and pretended I was Lucy. As far as identity wise, it was probably when I was around 10 and the neighborhood ladies told me how to look like a "knockout" after running around the neighborhood in an old dress.:)

[Taylor186]

Somewhere around 11-12. My mom had a skirted one-piece bathing suit in her bottom bureau drawer that I loved to wear when she went grocery shopping. She never caught me but at some point I remember looking for it and it was gone. Sad day, but I found other things to keep me happy.

[sissystephanie]

I think I was 6 when I first tried on a pair of my older sisters panties. But that was over 70 years ago, so I am not sure that was the right age!!:heehee:

[~Michelle~]

Some of you know what you did or how you felt when you were 4? :eek:

[Nicole Brown]

I really don't remember, but it must have been very early in life as I seem to remember always wearing woman's clothing. In fact, I cannot remember a time when I didn't wear them.

[Kate Simmons]

Some of you know what you did or how you felt when you were 4? :eek:Some things leave quite a lasting impression Michelle.:)

[StarrOfDelite]

I was about 6 or 7, and my cousin and her best friend, who were 3 years older, would dress me up in my cousin's old clothes. They would take all my clothes off down to the underwear, and usually managed to peek at my parts in the process, and then dress me up. I can remember being sexually excited, although I didn't understand what it was at the time. My aunt and mother never found out. I later had an affair with the best friend which started when we were drunk at my cousin's wedding. What goes around comes around?

I remember looking at some of my mom's clothes when I was a little older, but then gave it up for forty years. I didn't start dressing seriously until after I'd had a TV girl friend for several months, and persuaded her to makeup my face while I was wearing some of her clothes and one of her wigs. The rest, as they say, is history.

[Tiffany8]

I was about 12, Mom and dad went out to a dance or something and had left me alone for the first time. I was sneaking and snooping around the house for things that I knew were hidden ( $$, candy, gifts ... etc ). While looking in my parents room I came across my moms bra and underwear drawer. I can remember being interupted at that point by someone at the door. I closed the drawer and ran outta the room to answer the door. After they were gone I couldn't help but go back to the drawer and take a pair of my moms panties out and hold them up to me in front of the mirror. I liked what i saw and the felt so soft so I tried them on. :daydreaming: I believe I was hooked from then on.

I always looked forward to being left alone. as time went on I tried on her bras, then her slips and dresses. It wasn't long after that that my older sister moved back in with us. She wasn't home very often, but she had beautiful clothes that I kept stealing from her. Still don't think she ever realised it was me. I had taken so many pairs of nylons and panties and a couple bras too ( I can remember one red lacy top teddie she had ) :daydreaming:

Oh great, here comes that " pink fog " again, time to go get dressed.

[mohairfluffy]

When I was about 14 my mum had a beautiful red mohair sweater. I always wanted to wear it. When she was out I put on one of her baras and panties, packed out the bra with sox for titties, slip, skirt and the red mohair sweater. I had a hard on, it felt so nice as i caressed my fluffy breasts and then started to play with myself. I was in mums closet and felt like something was going to spurt out. The first thing i could grab was an orange mohair vest, i wrapped it around my member and spurted all i had, oh it felt so good.

I used to dress up and play whenever i could. Now i'm married i like to dress in my wifes clothes and play., she doesn't know. When ever i buy my wife clothes mostly but something i could wear too. Feels soo nice.

[fallen_rayne]

It was in High School, when I was dating my second boyfriend. I was the sub in the relationship and I loved it. So he asked me once how i would feel to dress up like a female one day.

My dirty little secret was stealing things from my older sister and wearing them around. So he opened the door for me and I jumped right on through. He said i was the cutest thing he ever saw, i never looked back. I don't date him anymore but we are still very very close friends. I even live with him right now. =3

[Elli87]

It started in preschool during playtime they had a bunch of old clothes. I would always dress up as a girl. Ive Been creeping around doing it ever since than.
My younger cousin knows but she's really cool with it. I drop little hints to the rest of my family all the time but they think I'm joking :tongueout