What was the first item you wore and at what age?

[purpleshiny]

I'm going to say lacy panties, and I'm going to say about three weeks ago.

[barby]

I was about 14.

Mom's blue denim skirt.

Mums nylon panties - 14 yo (they smelt & felt devine)

[Tiffanyfay]

My aunt 's Cathlic school socks at age 4.

[Sharon Anne McC]

*

This gets easy to answer.  I have memories to at least age three.  My sister is two years older than I and we wore the same size until I out-grew her when I got to be in my early 20s.

I had free access to my sister's clothes - anything from her dresser or closet - from age three.  As such, I wore anything that I chose (intimate-wear to outer-wear) and learned to wear whatever was appropriate as any girl.

It is amazing to think back to a time and place when children were safe when I was age 3 and age 4.  Or at least where we lived.  Or was it a matter of my parents being neglectfull according to today's concept?  My father worked full-time (aerospace) and my mother worked irregular hours in radio and TV (actress); my sister attended school (Kindergarten and 1st Grade).  They all left me home by myself to figure out how to make my own breakfast and lunch and dress myself for the day.  I recall one rare morning when my mom was home, but she was sloshed from the prior night's party; she was too drunk to help me tie my shoelaces, so my sister taught me that day.  Otherwise, I had free run of our home and where I went to play with neighbourhood friends.  If I chose to wear my clothes, then I did so; if I chose to wear my sister's clothes, then I did that.  If I wore from my sister's clothes, on cool days I wore her tights and on warm days I selected from her shorts or dresses.  It was all matter-of-fact.  Neither parent nor my sister were at home to tell me 'No'.  The other kids teased me but I did not really care.

I had little interest in my mother's clothes since they were too big.  I did not 'play dress-up' with her clothes.

Our parents divorced and our father got custody of us children when I was between 1st Grade and 2nd Grade (1963).

I had no clean white shirt for Catholic First Communion.  My paternal grandmother went to my sister's room and gave one of my sister's white blouses for me to wear.  My father raised no objection.  There I was wearing one of my sister's white blouses at my First Communion.

I had two older cousin's in their teen years while I was still young and learned how to do make-up at my aunt's home.  I visited with another cousin three years older for one Summer (1967); she had a swimming pool so I frequently tried on her bikini bathing suit and posed at the bathroom mirror.

As my sister got older and matured into puberty, so did I - in the sense that I surreptitiously grew into her adolescent clothes same time as she; that included bras, garter belts, and hosiery (pantyhose had not quite become commonplace in those days).  I discovered that I could have budding breasts as my sister - I filled balloons with water to match the size of her bra.  I could walk my residential neighbourhood in the evening and get mis-identified as my sister.

I frequently wore my sister's undies (7th Grade and 8th Grade years) on days when we had no PE and no fear of discovery at school.

I re-hemmed two of my sister's skirts to make them shorter to my liking (my 8th Grade).  To this day, she has never asked me if I did that.  Who else would have?

I bought my own female clothes for the first time when I was in 9th Grade.  It was easy - I told the saleslady it was for my mom's birthday.

The last time I wore my sister's clothes was 1977 (age 21).  By then I began secretly acquring my own female wardrobe during my final year residing with my father.  It became hide-and-seek as I'm certain he searched my bedroom for my female attire.  He may not have said anything specific when he surely found my female clothes (undies, tops, sweaters, dresses), but we surely had our heated words and worse with my on-going, now adult feminine protesting and his violent reactions.

*

[SueNZ]

Oh, Wow Sharon,
I am humbled by your self awareness and knowing who you really are.
You are an inspiration to all of us at our level of where we are at.
Due to years of hiding away and denial I have manifested an anti type viewpoint of those that do what I would like to have done i.e. pierced ears etc.
I am now working through slowly with my wife to break down those barriers and try to find who I really am. I am a little scared of where my limit will be and who I will be. We have discussed that I do like being a bloke but I would like to dress in female clothes all the time but since it is not possible to try and find a compromise somehow.
As an exciting step, my wife went yesterday to her wardrobe and has given me a lovely bright dress to wear at home so that I feel more comfortable on summer evenings (coming soon).

Thank you for sharing your story as it has helped me. 

[Kerry30Den]

That's great sue, that your wife gave you a summer dress!

I know that in my years of denial I'd developed these prejudices to help shield me from people discovering my secret.  It wasn't until I sorted out who I am that I have been able to initially recognize those pre judged notions and later toss them away.  I sometimes think I'm more of a whole person because of my dressing, but I think more accurately I've become a better person going through the process of accepting myself.  Acknowledging the things I like and owning up to it.

That learning who I am allowed me to share all of me with my spouse.  That honesty has brought us closer than most couples we know.

[TheMissingM]

I wore towels like my sisters when getting out of the baths when I was younger, folks thought it was kind of strange because I had 'no reason' to cover my entire body.

Probably actual article of clothing was my older sister's heels at 6... then I started to get more courage a year later and always doing it when I knew they were gone, surprisingly was never caught. At 7 I started wearing her dresses from when she was my age.. and as I got older, 9-10 I started wearing her jeans, tops, skirts, etc.. Parents never caught me so they never knew, well... they kind of knew when I had some dumb idea that gluing myself into shoes would force me to be caught..

To this day, they still have no idea it was me that did that.

Only started to buying my own 'female' clothes at around 19 years old, which thankfully for my small package and what not was Yoga pants, a sports bra and light t shirt.

[Kitty Pryde]

Ballet tights, at 5?

But for more serious, about a year ago, seamless boyshorts

[westin21]

Age 9 blue skirt set with white piping, leather boots and coat 

[BridgetYvonne]

Don't know if this is what got me started, but we had just moved to a new city & apt complex a few days before Halloween. I kept bugging Mom if she would get me a costume. She kept telling me that they had used all their money for rent, food etc. Finally at 430 on Halloween, Mom put her foot down & said "If you want to go trick or treating so bad, I can put you in your sister Shasta's clothes, & you go as a girl!" Well, you could have strip me naked, painted me blue & had me go as Naked Smurf. So Mom had me Nair shower & put out a pair of Shasta's underwear. After drying off, I peeked out to make sure Mom was the only one in the apt. I stepped out & she commented that I'd make a cute 4th Daughter. After putting her falsies in the bra, Mom had me put on one of Shasta's dresses & knee socks. As I sat there Mom applied makeup. As more & more of me went away & a girl appeared, I got kind of turned on. After she was done, she pinned her wiglet to my head, handed me a shopping bag & at 630 I was off. After the door slammed, reality hit. Cold October air hit my freshly shaved body & up my skirt. My eyelashes were heavy w/ mascara & every time I licked my lips, I tasted strawberry lip gloss. I took a deep breath & said Her goes nothing! I went along w/ a few parents & had the kids say "Trick or Treat" After 2 hours the pickings were kind of slim, so I went home. Totally forgetting I was 'en femme' I opened the door. There was Shasta & Cindy, my 2 older sisters. Plus 2 girls I never knew. Mom say me & said "So, Bridget. Aunt Jean says she'll pick you up in the morning. Share your candy!" My sisters caught on & didn't out me. I dumped out my candy, grabbed a few pieces & went in my room. After a half hour Shasta came in & I asked her if she wanted her clothes back? She went EWWWW Not now that my perv brother's been wearing them!" I don't have them any more. I guess I threw them out at my 1st purge about a year or so later. 

[Kimberley Beauregard]

Probably my v-neck long-sleeved top and skater skirt. This was last spring, so it would have been before I turned 26.

[Miril]

My sister's tights and tutu at the age of 5.   I think thats when my love of ballet started as well!

[TonyP]

Surprised that bras were not listed more.

[DawnOday]

About seven. Costumes costumes costumes. My Mom made costumes for my sister who was a dancer, drum major, baton twirler, actress.  She tried them on me and then put on rouge and lipstick and a little mascara. Then she would tell me how cute I looked.  My sister and I, when I came out to her a couple weeks ago agreed that Mom was weird.  You know if it's the only thing you've  been praised for, you continue to hunger the attention. Somehow for the short time I get dressed, I feel all the stress drifting away. I like what I see in the mirror, and somehow liberated from all the male macho hocus pokus. I like a good cry. I love taking care of babies. I love talking to women about their clothes, hair and makeup. I like the way women smell, I like the way they laugh. I like that they can small talk. We guys don't do that much.

[Alana74]

I think it was a pair of my mother`s shoes that I first tried . I can`t remember exactly what age it was though

[whorton59]

Officially the first womens/girls thing I ever put on was a multi color bikini of my cousins at age 12 back in 1971. . .

As it was not very practical, I borrowed a bra and panties from my girlfriend. size 34B and size 7 panties. .IIRC in 1974 while going to night school I remember wearing panties under jeans to night school . . The rest is history. . .

[Daphnelove]

I was 17. It was my Mom's long black evening gown. It's kind of her go to dress for special events (weddings etc) not sure if it was the absolute 1st but it was during my first "session" its still my absolute favorite makes me feel glamorous as hell!

[soyun.sa]

I was about 8 or 9, and my mum had the most fab thigh high boots with a tiny kitten heel on them, they were fur lined and black letherish material. I would pick up a the thin piece of mdf that mum used to do her puzzles on and strut my stuff as if I was the most important person in the world, an attitude to which I still hold.

I guess that's where my love of shoes and heels began.

[Karen6-10inheels]

Dress and everything. Mom dressed me up as a girl at 5. I looked so cute I have the pic from way back. I guess what I put on myself, moms panties.

[Alex123]

My sisters clothes from the age of 5.  My mum let me sleep in nighties (at my request) up until the age of 10.