Susan's Place Transgender Resources

Community Conversation => Crossdresser talk => Topic started by: leatherdres5 on July 21, 2015, 12:53:04 pm

Title: What was the first item you wore and at what age?
Post by: leatherdres5 on July 21, 2015, 12:53:04 pm

I was about 14.

Mom's blue denim skirt.

Title: Re: What was the first item you wore and at what age?
Post by: Allison Wunderland on July 21, 2015, 01:19:21 pm

Bath towels as skirts, about 4 yrs. old. And so, is it trans, cross, ambiguous, or sometimes a towel is simply a towel, to paraphrase Freud.

Title: Re: What was the first item you wore and at what age?
Post by: Aeirs on July 22, 2015, 11:36:14 pm

Panties jeans and bra that I took when my mom was gone when I was 15

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Title: Re: What was the first item you wore and at what age?
Post by: ToniB on July 23, 2015, 02:01:06 am

My sisters dresses and Panties at about 7 Years old

Title: Re: What was the first item you wore and at what age?
Post by: Yenneffer on July 23, 2015, 02:21:01 am

Alice in wonderland costume at age 3

Title: Re: What was the first item you wore and at what age?
Post by: Cindy on July 23, 2015, 02:59:55 am

A nappy and blanket when I was born?

can't say I remember it :laugh:

Title: Re: What was the first item you wore and at what age?
Post by: Kayleewantsout on July 23, 2015, 06:18:44 am

9 and underwear

-Kaylee

Title: Re: What was the first item you wore and at what age?
Post by: Marlee on July 23, 2015, 07:04:38 am

I was prolly about 6 or 7 and I put on my mom's clip-on earrings.

Title: Re: What was the first item you wore and at what age?
Post by: leatherdres5 on July 23, 2015, 01:17:07 pm

Thank you for reminding me.....

I used to wear mom's clip-on earrings.

Title: Re: What was the first item you wore and at what age?
Post by: Joi on July 24, 2015, 12:37:34 am

My younger sister's dress. 8 yrs. old.

Title: Re: What was the first item you wore and at what age?
Post by: Mado G on July 24, 2015, 01:27:49 am

At about 11, I pinched a pink kilt from my sister. I remember once wearing it while using the computer, when my dad came in suddenly, startling me. I was terrified he'd seen it, but he never said anything.

Title: Re: What was the first item you wore and at what age?
Post by: BirlPower on July 24, 2015, 07:05:09 am

swapped panties with the daughter of a friend of my parents during a sleepover. Age 4 I think.

Title: Re: What was the first item you wore and at what age?
Post by: Stevie on July 24, 2015, 11:32:49 am

  I think I was about 7 or 8, there was a box of my older sisters old clothes in the garage. I remember one white dress that was my favorite I was very sad when I out grew it.

Title: Re: What was the first item you wore and at what age?
Post by: Jacqueline on July 24, 2015, 12:55:00 pm

8 or 9 YO.

Tried my Mom's but moved to my sisters underwear, slips and hose. Then tried on skirts and dresses and bathing suits.

Loved it, hated myself at the time and did not quite get any of it.

Joanna

Title: Re: What was the first item you wore and at what age?
Post by: CarlyMcx on July 24, 2015, 05:07:30 pm

Scrunched and rolled my Fruit of the Loom underwear down into bikini panties when I was five.  Mom never had anything that interested me and my only sister was a lot younger than I was, so there was nothing to steal or borrow.  My first "real" crossdressing was a bikini I mail ordered when I was 20.

Title: Re: What was the first item you wore and at what age?
Post by: Willowicious on July 24, 2015, 05:38:54 pm

Mother's bra at age 3

Title: Re: What was the first item you wore and at what age?
Post by: kittenpower on July 24, 2015, 06:27:00 pm

...diapers, when I was a newborn, IIRC  ;D

Title: Re: What was the first item you wore and at what age?
Post by: Kerry30Den on July 26, 2015, 02:54:07 pm

Pantyhose at the age of 4 or 5.  Found some in a bag and tried them on and I was hooked.   Started me down my path in life.   Fought it for years but finally accepted it around 30 and been happier since.

Title: Re: What was the first item you wore and at what age?
Post by: gennee on July 26, 2015, 07:50:53 pm

My wife's skirt-at age 56.

 :)

Title: Re: What was the first item you wore and at what age?
Post by: janetcgtv on July 26, 2015, 08:22:18 pm

When I was 7 in the 1950's while living in Chicago I was under my front porch and asked my friend if I could wear her babushka and she let me. I loved every moment of it. When older I would buy my own babushkas.

Everyone have a lovely day.
Before that when I was 3, I had put on my mothers perfume.

Title: Re: What was the first item you wore and at what age?
Post by: missymarieme on July 27, 2015, 10:07:51 pm

At 6 I would take my sister's underclothes and her dresses as I grew I'd take more bras panty hose,

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Title: Re: What was the first item you wore and at what age?
Post by: Seana69 on July 28, 2015, 10:43:50 pm

I was about 9 yrs old, I had some alone time, I put on my mom's girdle and stockings she had just taken off after work
I felt so girly and nice.. I was confused as to why but  well we all know the story

Title: Re: What was the first item you wore and at what age?
Post by: KatelynBG on July 31, 2015, 01:48:31 pm

My mom's shiny white 80s-tastic dress age 9ish. My mom was the only woman in the household and her fashion was kind of depressing but I'll never forget that white dress with hip flares and shoulder pads.

Title: Re: What was the first item you wore and at what age?
Post by: Northern Jane on August 01, 2015, 06:47:35 am

Clothing didn't matter too much to me when I was young. When and where I grew up, many of the girls wore the same shirt and jeans as the boys and most rolled up the bottom of the shirt and tied it at the waist so that's what I did too. It wasn't until my early teens that I started buying female-specific clothes. The "Uni-sex" fade came at just the right time for me LOL!

Title: Re: What was the first item you wore and at what age?
Post by: SarahMarie1987 on August 01, 2015, 12:50:00 pm

Hmmm.

I was about 12-13, and I wore a top, and black tights with heels. I do remember trying on one of my sisters' bras.

Title: Re: What was the first item you wore and at what age?
Post by: Danielle89 on August 01, 2015, 06:53:29 pm

At 7, A red dress of my cousin. When I visited my uncle's house. After taking bath, I didn't have any clothes to wear, so my cousin gave me this dress  ;)

Title: Re: What was the first item you wore and at what age?
Post by: sweetbriar9 on August 16, 2015, 07:03:06 pm

Towels, blankets, and whatever early on. At about 9 I found a pretty fabulous high waisted two piece bathing suit from the fifties. Yellow with white fishnet over it. So sad when I outgrew it. Vintage style has always been my favorite.

Title: Re: What was the first item you wore and at what age?
Post by: SueNZ on August 16, 2015, 07:19:22 pm

11 years. My mothers Bra, slip, skirt and pantyhose plus lipstick. My mother was the only girl in our house of 6. I had only fleeting moments to do this.

Title: Re: What was the first item you wore and at what age?
Post by: cheryl reeves on August 17, 2015, 10:33:13 am

my mom wanted her firstborn to be a girl so she went and bought girl clothes and when i was born a month early and was a boy she had no boy clothes so she dressed me as a girl til my dad put a stop to it when i was 3. what i was thankful for was gender neutral clothing til i was 13 and started to get into my middle sis underthings,then at 17 started to wear my moms dresses when i was home alone..

Title: Re: What was the first item you wore and at what age?
Post by: Breanna93 on August 22, 2015, 10:15:14 am

Mom's one piece panty /bra /girdle combo, age 9.
Then anything (of mom's) I could get my hands on  >:-)  >:-)  >:-)
Don't know why, though I'd gone crazy, ashamed, inbarested, but just couldn't stop.

Title: Re: What was the first item you wore and at what age?
Post by: Ciara on August 23, 2015, 06:21:48 am

I really don't recall the first item. It was over 50 years ago and it was my sister's clothing. To be honest I've been wearing women's clothes since as long as I can remember 😌😌.
Ciara.

Title: Re: What was the first item you wore and at what age?
Post by: Traci New on August 23, 2015, 07:32:51 am

panites i was about age 5

Title: Re: What was the first item you wore and at what age?
Post by: Sandy74 on August 29, 2015, 06:41:18 am

I think I was around ten or eleven and snuck into my older sisters room and tried on one of her dresses and looked at myself in the mirror and twirled around modeling in front of the mirror, it wasn't a sexual high at the time but once I discovered her underwear drawer that totally changed and I got very aroused by slipping on a pair of her panties. I thought they were the most comfortable article of clothing ever and I still do. I always got jealous that girls had such amazing underwear.

Title: Re: What was the first item you wore and at what age?
Post by: Richenda on August 29, 2015, 11:23:49 am

Went into the airing cupboard to pull out my sister's knickers. Put them on and had such a buzz.

I was 4.

:)

Title: Re: What was the first item you wore and at what age?
Post by: Devlyn on August 29, 2015, 11:40:00 am

This dress, at 46.

[Image Removed]

Title: Re: What was the first item you wore and at what age?
Post by: KathyLauren on August 29, 2015, 07:18:42 pm

My mother's underwear, age 12.

Title: Re: What was the first item you wore and at what age?
Post by: Yuko on September 04, 2015, 07:49:03 am

Nylons…  I have three amazing nylon memories…. first time I felt them on a girl friend, first time I tried them on, and the first time I had enough courage to buy some for myself.

Title: Re: What was the first item you wore and at what age?
Post by: LizK on September 04, 2015, 09:48:52 am

My cousins party dress that she should have been wearing, instead I was much to countenance of all the adults. Don't remember how it happened had to have been about 6 or 7

Title: Re: What was the first item you wore and at what age?
Post by: rachel89 on September 05, 2015, 11:23:38 pm

Women's underwear. Age 19

Title: Re: What was the first item you wore and at what age?
Post by: Joi on September 06, 2015, 12:05:47 am

I can remember trying on some of my "great-aunt's" underwear when I was about 10.  It is still so clear in my mind that it could have been yesterday.  My gender dysphoria had already been triggered a couple of yrs. earlier.  This would have been in the mid '50's and my great aunt was already old (to me) by then, probably in her mid 50's.  I found the underwear stored in an old trunk in her attic. What was great about it was that they were so pretty and were pantelettes (mid thigh fitting.)  She would have worn them when she was in her late teens or early 20's.  That would have been in the "Roaring 20's."  Sure wish I had them now!

Title: Re: What was the first item you wore and at what age?
Post by: purpleshiny on September 07, 2015, 01:52:42 pm

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

Title: Re: What was the first item you wore and at what age?
Post by: barby on September 09, 2015, 03:04:55 am

Quote from: leatherdres5 on July 21, 2015, 12:53:04 pm

I was about 14.

Mom's blue denim skirt.

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

Title: Re: What was the first item you wore and at what age?
Post by: Tiffanyfay on September 09, 2015, 04:20:37 am

My aunt 's Cathlic school socks at age 4.

Title: Re: What was the first item you wore and at what age?
Post by: Sharon Anne McC on September 09, 2015, 08:31:16 am

*

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.

*

Title: Re: What was the first item you wore and at what age?
Post by: SueNZ on September 09, 2015, 01:54:29 pm

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.  ;) :angel:

Title: Re: What was the first item you wore and at what age?
Post by: Kerry30Den on September 10, 2015, 01:59:10 pm

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.

Title: Re: What was the first item you wore and at what age?
Post by: TheMissingM on September 11, 2015, 02:58:44 am

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.

Title: Re: What was the first item you wore and at what age?
Post by: Kitty Pryde on September 11, 2015, 11:08:37 pm

Ballet tights, at 5?

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

Title: Re: What was the first item you wore and at what age?
Post by: westin21 on October 13, 2015, 09:41:50 am

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

Title: Re: What was the first item you wore and at what age?
Post by: BridgetYvonne on October 13, 2015, 12:23:22 pm

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. 

Title: Re: What was the first item you wore and at what age?
Post by: Kimberley Beauregard on October 13, 2015, 12:44:57 pm

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

Title: Re: What was the first item you wore and at what age?
Post by: Miril on October 15, 2015, 08:00:14 pm

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

Title: Re: What was the first item you wore and at what age?
Post by: TonyP on March 15, 2016, 02:52:09 pm

Surprised that bras were not listed more.

Title: Re: What was the first item you wore and at what age?
Post by: DawnOday on March 15, 2016, 06:14:41 pm

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.

Title: Re: What was the first item you wore and at what age?
Post by: Alana74 on March 16, 2016, 01:12:21 am

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

Title: Re: What was the first item you wore and at what age?
Post by: whorton59 on March 16, 2016, 02:53:51 pm

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. . .

Title: Re: What was the first item you wore and at what age?
Post by: Daphnelove on March 29, 2016, 01:51:48 pm

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!

Title: Re: What was the first item you wore and at what age?
Post by: soyun.sa on March 31, 2016, 03:45:24 pm

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.

Title: Re: What was the first item you wore and at what age?
Post by: Karen6-10inheels on March 31, 2016, 07:17:15 pm

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.

Title: Re: What was the first item you wore and at what age?
Post by: Alex123 on May 06, 2016, 04:56:50 am

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

Title: Re: What was the first item you wore and at what age?
Post by: chris.deee on May 07, 2016, 03:42:04 pm

First was my grandmother letting me play with her jewelry at her apartment around 7.

After that, it was a towel plus using bath crayons as makeup in private around 10.

First wore a bra and got dressed at 12 when my mom started going back to work. 

I bought my first pair of heels at 23 and switched to having my own wardrobe by 26 when I came out to my wife.

Title: Re: What was the first item you wore and at what age?
Post by: Rafaela on May 07, 2016, 05:27:05 pm

a pair of stockings at around 5 or 6. I remember loving how smooth and nice they felt, and rolling around in my parents' bed. When she came in and found me it was weird  ??? ???
Haven't worn anything like that in a looooong time.

Title: Re: What was the first item you wore and at what age?
Post by: BeverlyAnn on May 07, 2016, 07:46:22 pm

Panties and I don't even know how old I was.  I only have faint memories of it and it was kind of strange circumstances.  I was in a day care and I guess during nap time I had an accident.  Since it was long before the days of health codes, the day care actually had spare underwear for when kids had those accidents.  You would wear them home and your mom washed them when she did the laundry and then bring them back.  The day it happened to me, the only underwear they had in the cabinet was girls panties.  Like I say, I don't remember a lot about it but I do remember when I put the panties on, everything was right with the world and this was something I was supposed to be wearing. 

Title: Re: What was the first item you wore and at what age?
Post by: possiblyrhianne on May 12, 2016, 06:40:55 am

I had to wear tights for a school play. Was embarrassed at the time.

If only I knew what I did now hahah....

Title: Re: What was the first item you wore and at what age?
Post by: bree_davis01 on May 12, 2016, 02:45:03 pm

let's 12ish? wearing a dress my mom was getting ride of. after being caught by my sister, she shared cloths

Sent from my SM-G900V using Tapatalk

Title: Re: What was the first item you wore and at what age?
Post by: AxelM07 on May 21, 2016, 07:23:17 pm

I guess I was about 12, and I wore one of my sister's guy shirts.

Title: Re: What was the first item you wore and at what age?
Post by: Alex Forbes on June 08, 2016, 01:19:35 pm

My cousin's black opaque tights. I think I was 12.

Title: Re: What was the first item you wore and at what age?
Post by: jacquelynh on June 09, 2016, 06:02:02 am

A dress my mom made me try on,I was 7 or 8 years old when this happened.My mom thought I looked cute in it

Title: Re: What was the first item you wore and at what age?
Post by: Elli.P on June 09, 2016, 06:15:37 am

Mom's bra, age 6. Was in the bathroom before bathing. She had D cups and walked in while I was trying to stuff dirty clothes into it to fill the cups. She was very angry and yelled at me to never do it again. But I kept doing it just didn't  get caught anymore.

Title: Re: What was the first item you wore and at what age?
Post by: FrancisAnn on June 09, 2016, 08:09:59 am

That's funny. I loved to play dress up like any little girl would, age 4-5 I guess, red lipstick & red nail polish were so cool & my little feet in my moms high heels. My mom was OK with it but my father was not pleased. Oh & I loved pearl necklaces....any jewelry. Those were great days before my first grade teacher told me I was a boy...ugggg, she was so wrong but I was forced to act kinda like a boy, booooooooooooo.

Title: Re: What was the first item you wore and at what age?
Post by: DianeofCarlsbad on June 17, 2016, 12:58:46 pm

I know it was pre kindergarden, so 4 maybe 5 years old. Even after all these years I still remember putting on a pair of my mom's high heels. They were navy blue peep toe pumps. Standing up in them was just such a wonderful feeling. Shortly after that I began wearing her dresses along with the heels.

My mom was a nurse who worked nights so I think anything that could keep me busy while she sleep was ok with her

Title: Re: What was the first item you wore and at what age?
Post by: Thea on June 17, 2016, 01:05:41 pm

As a kid, I was always being mistaken for a girl. In the summer of 1972, when I was 12 years old, my older cousin asked if I would go to the mall with her to do some shopping. When I came out of my room in a halter top, short shorts and girly flip-flops, she was a bit surprised but accepted me as I was. She was a good friend then, and a great lady now. To this day, she's the only family member I have that knows my little secret.

Title: Re: What was the first item you wore and at what age?
Post by: FrancisAnn on June 17, 2016, 02:16:14 pm

Those were fun days at 4-5 years old wearing my mom's high heels. They felt great & I was such a happy little girl.

Title: Re: What was the first item you wore and at what age?
Post by: kylie1 on June 19, 2016, 09:41:19 pm

I started with my sisters panties and moms lipstick when I was four.  I felt at home. I even wore my sisters panties to school on and off starting in the first grade.

Title: Re: What was the first item you wore and at what age?
Post by: GdsMichelle on June 21, 2016, 10:12:47 pm

20 years old barrow my aunts clothes for Halloween costume.

Title: Re: What was the first item you wore and at what age?
Post by: Dee Marshall on June 22, 2016, 05:43:56 am

Quote from: GdsMichelle on June 21, 2016, 10:12:47 pm

20 years old barrow my aunts clothes for Halloween costume.

Goodness! You reminded me...
One year when I was in grade school, perhaps second or third grade, my mother made a ghost costume for me for Halloween. We used to wear our costumes to school and mine came home dirty and ripped. Mind, at that age I didn't know I was trans, no one knew what is was and if I ever had known it was bullied out of me long before.

At the last minute all my mom could think of was to dress me as a little old lady, dress, heels, makeup, hat with veil and all. I had a great time and loved the costume. I guess a cis boy would have been embarrassed and would have refused to go out trick-or-treating.

Should have guessed then and there.

Title: Re: What was the first item you wore and at what age?
Post by: Vanessa2016 on June 28, 2016, 10:16:47 pm

Sisters bra and panties at about 10 years old

Title: Re: What was the first item you wore and at what age?
Post by: cdjenna69 on July 04, 2016, 10:09:27 am

when I was 13 years old I found a bag with girls clothes in it. the first thing I put on was a black skirt and pink panties.

Title: Re: What was the first item you wore and at what age?
Post by: Amy Chislett on July 04, 2016, 04:59:48 pm

Two accidental incidences earlier: ten years old, Halloween - not my idea - done up extensively but as an older matroness.  At 23, was having passionate argument with rooms, they were gone, the rented place was filled with stuff - found a polyester white flower dress and put it on for kicks.

And then this first week of April was the first time I took my place in the bedroom and mail ordered black lace stockings w attached garter.  I'm 51.

Title: Re: What was the first item you wore and at what age?
Post by: FrancisAnn on July 05, 2016, 05:18:44 am

Gosh, age 4-5 everything of my mom's I loved to play dress up in her heels, red lipstick, red nail polish. I was just a normal little girl. I've always been female & so glad for that.......

Title: Re: What was the first item you wore and at what age?
Post by: V M on July 05, 2016, 05:59:38 am

My mother dressed me in one of my sister's outfits when I was about 4-5 to prove some sort of point I didn't understand the time but then she became dismayed when I was rather happy about it and wanted to go show my friends

I darted out the door and was half way down the street before she could put the grab on me and carry me home kicking and screaming

If I remember right it was a lovely powder blue dress with black patent shoes

I thought I looked great

Title: Re: What was the first item you wore and at what age?
Post by: Jacqueline on July 11, 2016, 01:22:28 pm

Quote from: Amy Chislett on July 04, 2016, 04:59:48 pm

Two accidental incidences earlier: ten years old, Halloween - not my idea - done up extensively but as an older matroness.  At 23, was having passionate argument with rooms, they were gone, the rented place was filled with stuff - found a polyester white flower dress and put it on for kicks.

And then this first week of April was the first time I took my place in the bedroom and mail ordered black lace stockings w attached garter.  I'm 51.

Wanted to welcome Amy to the site. You and I are about the same age. It has been a tough path but it can help you in the long run.

I also want to share some links with you. They are mostly welcome information and the rules that govern the site. If you have not had a chance to look through them, please take a moment:

Things that you should read

Site Terms of Service & Rules to Live By (https://www.susans.org/forums/index.php/topic,2.0.html)	Standard Terms & Definitions (https://www.susans.org/forums/index.php/topic,54369.0.html)	Post Ranks (including when you can upload an avatar) (https://www.susans.org/forums/index.php/topic,114.0.html.)
Reputation rules (https://www.susans.org/forums/index.php/topic,18960.0.html)	News posting & quoting guidelines (https://www.susans.org/forums/index.php/topic,174951.0.html)	Photo, avatars, & signature images policy (https://www.susans.org/forums/index.php/topic,59974.msg383866.html#msg383866)

Once again, welcome to Susan's. Look around, ask questions and join in.

With warmth,

Joanna

Title: Re: What was the first item you wore and at what age?
Post by: Heather14 on July 15, 2016, 06:37:33 pm

I was around 8. I would put my moms panties, bra, garter belt and stockings on. They felt wonderful and I felt normal. I found that I couldn't wait till I was at home alone so I could raid her closet. I love the feel of women's clothes and lingerie.

Title: Re: What was the first item you wore and at what age?
Post by: Jacqueline on July 15, 2016, 09:25:45 pm

Heather,

I wanted to welcome you to the site too.

If I could direct you to the welcome note above your post. I sent it to Amy. Please assume it is to you as well. The links are kind of important.

Hope you enjoy your time here and find what you are looking for.

With warmth,

Joanna

Title: Re: What was the first item you wore and at what age?
Post by: Heather14 on July 16, 2016, 06:51:09 am

Thank you Joanna, I will go through the links today. I am happy to have found this site and look forward to being a member.

With kindness,
Heather

Title: Re: What was the first item you wore and at what age?
Post by: Elena1270 on August 07, 2016, 02:27:42 pm

My mothers knee highs. I think I was around 5.

Title: Re: What was the first item you wore and at what age?
Post by: christinefornow on August 16, 2016, 12:42:43 pm

We had a laundry chute down to the basement so I had so many to choose from. But the very first was panties and bra.

Title: Re: What was the first item you wore and at what age?
Post by: Alice-jones on August 16, 2016, 03:20:29 pm

I was about 7-8 and it was my moms black boots

Alice s

Title: Re: What was the first item you wore and at what age?
Post by: spx_1112 on August 17, 2016, 08:37:58 am

Bra Panty Pantyhose

Title: Re: What was the first item you wore and at what age?
Post by: Bobbie1952 on August 18, 2016, 11:00:59 am

When I was five, my cousins dressed me up in one of their old dresses.  A whole outfit really, panties, slip, anklet socks, and shoes.  My mom loved her new daughter and let my cousins dress me up all the time.

Title: Re: What was the first item you wore and at what age?
Post by: Veronique10 on September 19, 2016, 10:10:08 pm

Quote from: Northern Jane on August 01, 2015, 06:47:35 am

Clothing didn't matter too much to me when I was young. When and where I grew up, many of the girls wore the same shirt and jeans as the boys and most rolled up the bottom of the shirt and tied it at the waist so that's what I did too. It wasn't until my early teens that I started buying female-specific clothes. The "Uni-sex" fade came at just the right time for me LOL!

Similar experience for me. Pre-teen clothing didn't matter because girls and boys dressed very similar. (This wasn't in the Unted States.) That said, when I was a toddler, my mother dressed me in things that were decidedly girlish. I was mistaken for a girl throughout my childhood and teenage years. During my pre-teen years, I spent a fair amount of time both in public and in private roleplaying with boys, where I was always the "girl" role. Since opportunities to be the girl presented themselves, needing clothing specific to the mode wasn't neccessarily a preoccupation.   

The first time I can remember actually wanting to wear girls glothes was around age 12. I became more self aware of a desire to continue in the "girl" mode of my roleplaying and times when I was mistaken for a girl. It started with a fascination with my mother's, sister's and aunt's clothing. (I grew up in a predominantly female home.) Actually wearing girl clothes was in trying on those of my sister's best friend, who lived with us for a while. The friend was my size and used to joke about us being able to "share clothes." I fit into her tops and very snug jeans and undies. It felt totally natural for me.

Title: Re: What was the first item you wore and at what age?
Post by: biannne on October 04, 2016, 12:07:09 am

I was only 10 years old when I found my mom old mini skirt that she had thrown in the basement.

Title: Re: What was the first item you wore and at what age?
Post by: Mohini on October 04, 2016, 01:09:01 pm

I would say I was about seven years old when the school staff dressed me up as an angel for the Christmas play at the school for the deaf.  I don't know what was going on.  I must have been an extra on stage, because I couldn't really speak very well, having entered the school 3 months before.  Imagine that!  I was dressed as a girl by school staff!  How advanced they were for the 70s!   :laugh:

If you mean "voluntarily," that would be about 12-13 years old with a pair of panty hose...

Title: Re: What was the first item you wore and at what age?
Post by: Christine_Hart on October 04, 2016, 02:59:51 pm

10 or 11 trying on a bra after sneaking into bedroom at house family were visiting. Just assumed it was something all young boys did although have tried to analyse it once or twice given later life developments. No great conclusions though.

Title: Re: What was the first item you wore and at what age?
Post by: Virginia Hall on October 04, 2016, 03:11:53 pm

At 4. A skirt.

Title: Re: What was the first item you wore and at what age?
Post by: valerie anne on October 04, 2016, 03:13:48 pm

At about the age of 12, my best friend and myself sneaked into his house. We got one of his mum's bras and I gagged to put it on. As I remember, it wasn't a bad fit, so maybe it was meant to be.

Then he made me up with red lipstick and he dived for my bra. He slipped down my strap and really latched onto my left nipple. I was in heaven and I held him close to me.

Since then I have always wanted to be a woman with boobs who could breast feed.

Title: Re: What was the first item you wore and at what age?
Post by: Shawnadj on October 09, 2016, 08:53:26 am

A top and skirt my mom had me put on and this was when I was 8 years old.

Title: Re: What was the first item you wore and at what age?
Post by: Christine_Hart on October 09, 2016, 09:44:00 am

Quote from: valerie anne on October 04, 2016, 03:13:48 pm

At about the age of 12, my best friend and myself sneaked into his house. We got one of his mum's bras and I gagged to put it on. As I remember, it wasn't a bad fit, so maybe it was meant to be.

Then he made me up with red lipstick and he dived for my bra. He slipped down my strap and really latched onto my left nipple. I was in heaven and I held him close to me.

Since then I have always wanted to be a woman with boobs who could breast feed.

Blimey! Did the two of you talk about it later or did anything else happening?

Title: Re: What was the first item you wore and at what age?
Post by: Sixpac2k on July 30, 2019, 09:07:54 am

Pantyhose age 13 I also started wearing a cup with them because it made a smooth lump. If I was home alone I would put them on and sit in the basement and look at .myself  thinking how cool would it be to have a smooth front

Title: Re: What was the first item you wore and at what age?
Post by: SheShe on August 06, 2019, 11:01:24 pm

I would dig into my mothers stuff when she was in the kitchen cooking, my favorite was her girdle for some reason.   I was around 6 or so and my parents knew of my interest and took me to a shrink and after a few meetings that was the end of that.   I guess the shrink told them that I would grow out of it,,ha ha little did he know.

Title: Re: What was the first item you wore and at what age?
Post by: DebraM on August 14, 2019, 08:26:43 am

36,My wife's blue dress.My wife opened up her closet letting me pick out something to try on.I loved it and she said I looked good in it.

Title: Re: What was the first item you wore and at what age?
Post by: KathyLauren on August 15, 2019, 06:24:29 pm

Quote from: SheShe on August 06, 2019, 11:01:24 pm

I would dig into my mothers stuff when she was in the kitchen cooking, my favorite was her girdle for some reason.   I was around 6 or so and my parents knew of my interest and took me to a shrink and after a few meetings that was the end of that.   I guess the shrink told them that I would grow out of it,,ha ha little did he know.

Hi, SheShe!

Welcome to Susan's Place.

Normally we try to catch new members right away to give them an official welcome.  Sorry that you apparently got missed when you first arrived.

Better late than never, here is your official welcome...

Please feel free to stop by the Introductions forum (https://www.susans.org/forums/index.php/board,8.0.html) to tell the members about yourself.  Here is some information that we like to share with new members:

Things that you should read

Site Terms of Service & Rules to Live By (https://www.susans.org/forums/index.php/topic,2.0.html)	Standard Terms & Definitions (https://www.susans.org/forums/index.php/topic,54369.0.html)	Post Ranks (including when you can upload an avatar) (https://www.susans.org/forums/index.php/topic,114.0.html.)
Reputation rules (https://www.susans.org/forums/index.php/topic,18960.0.html)	Cautionary Note (https://www.susans.org/forums/index.php/topic,82221.0.html)	Photo, avatars, & signature images policy (https://www.susans.org/forums/index.php/topic,59974.msg383866.html#msg383866)

Title: Re: What was the first item you wore and at what age?
Post by: chloe_h on August 15, 2019, 06:33:54 pm

I didn't think I'd remember because it's such a long time ago but it came right back to me. My mother's shoes. Tan leather pumps with a low heel. I would have been very young, surely under five, so they were much too big but I loved them. And after that, her jewelry (I still adore jewelry :) )

Title: Re: What was the first item you wore and at what age?
Post by: Allie Jayne on August 15, 2019, 09:10:47 pm

Age 4, I snuck my aunties red short sexy babydoll into the laundry and put it on. At that instant I was sure I was born into the wrong body, and 61 years later I am waiting for HRT to correct that!

Allie

Title: Re: What was the first item you wore and at what age?
Post by: Stevenator on September 12, 2019, 01:00:25 am

My mom’s Satin Full Slip. I think I was 9.

Title: Re: What was the first item you wore and at what age?
Post by: LaRae on September 12, 2019, 11:15:31 am

Me & my ex-boyfriend wore full 'drag' for halloween in '16. He kind of goofed it & ended up looking more like a giant, purple Riding Hood more than anything. I, on the other hand, had a very deeply hidden agenda to take it seriously, push it & see how it would look.

Once it was on, I didn't have some huge revelation, just felt extremely comfortable, didn't care at all (which should've been a red flag moment in itself, lol).

Title: Re: What was the first item you wore and at what age?
Post by: michele4848 on September 18, 2019, 03:18:44 pm

I was 8yrs old.  I wore my mothers seamed hose, garter, panties and bra, all in white. got caught several times and whipped several times.  later I found a suitcase by the highway and it had several sets of girls clothes. I had a out door hideout that only 3 people knew. I used to dress up for a boy I knew and for a while I got to be his girl, in a sexual way .  its funny really, my mother always disliked me and said I was supposed to be a girl and I ruined her life. go figure.  I always wished I could be close to my mother and have a deep relationship that only a mother-daughter have.

Title: Re: What was the first item you wore and at what age?
Post by: deanna7506 on September 26, 2019, 10:37:50 pm

My mom's one piece bathing suit in sixth grade

Title: Re: What was the first item you wore and at what age?
Post by: JaimeL71 on October 09, 2019, 02:50:23 pm

Quote from: deanna7506 on September 26, 2019, 10:37:50 pm

My mom's one piece bathing suit in sixth grade

Same except it was my older sister's one piece.  It wasn't even an urge to crossdress, but a genuine curiosity of how something that looked so small fit on her body.  Even after all these years, I can still remember the (surprise) feelings it gave me once it was on.  Even though they aren't practical, I still have a weakness for one-piece swimsuits to this day.

Title: Re: What was the first item you wore and at what age?
Post by: Sophiaprincess2019 on October 09, 2019, 06:32:43 pm

10 y.o. sisters panties...they were big on me (she's older) followed by Mom's pink robe. I wore Mom's robe around the house until I was 15 or so.

Sophia

Title: Re: What was the first item you wore and at what age?
Post by: Ciara on October 10, 2019, 06:18:13 am

Quote from: DebraM on August 14, 2019, 08:26:43 am

36,My wife's blue dress.My wife opened up her closet letting me pick out something to try on.I loved it and she said I looked good in it.

@Debra
You must have an amazing wife.
Ciara

Title: Re: What was the first item you wore and at what age?
Post by: Stephaniesteve on October 21, 2019, 05:34:54 pm

I wore my female cousins panties and skirt and pyjamas when I was 5.
It was also the time I saw how different she was between the legs and knew that I had got the wrong bits there. I was hooked for life.
Stephanie

Title: Re: What was the first item you wore and at what age?
Post by: Mills on November 25, 2019, 02:02:36 am

I was six, my sister had a couple of new nightdresses, one of them had Tinkerbell on it and she didn't like it but I did so I wore it after a bath, it was on a bannister opposite the bathroom door I picked it up and put it on, people were shocked, I wore it 'till it didn't fit any more, I still have it somewhere.

Title: Re: What was the first item you wore and at what age?
Post by: Adrianna40 on November 25, 2019, 06:23:41 am

My first attempt,my friend Nikki's red dress,I was 16 at the time.My wife knows this,I told her it.

Title: Re: What was the first item you wore and at what age?
Post by: Haley Conner on November 25, 2019, 06:53:50 am

A friends swimsuit, age 8 or so, I think.

Title: Re: What was the first item you wore and at what age?
Post by: MaryT on November 25, 2019, 10:30:01 am

I remember that when I was about 4, I used to put on my mother's headscarf and look in the mirror.  I wanted to be like the other girls, so I liked hiding my short hair.  Where possible, I wore nothing else, as I hated boys' clothes for the same reason.  (Until I was 8, I didn't know that girls didn't have willies, so I didn't realise that being naked sort of emphasised that I was AMAB.  My mother said that she knew I was a boy because of my teeth.)  I sometimes wore a towel wrapped like a dress or kanga.

My mother told me that when I was a baby, she dressed me in baby girls' dresses (layette, I think Americans say).  She said that many mothers did it because it was easier to access nappies, etc.. 

Title: Re: What was the first item you wore and at what age?
Post by: JennyTG on January 19, 2020, 09:01:38 pm

Can't say for sure but most probably my Mum's full slip, it felt utterly heavenly as well.  I knew I'd be addicted from that moment on, around 14 I'd say.

Title: Re: What was the first item you wore and at what age?
Post by: Heather N on January 21, 2020, 09:27:03 am

for me , it was Halloween in 6th grade. My mom dressed me up and I did it several times after that, as I grew a bit older I would snag some of my sisters clothes as she outgrew them. I got caught by my father and I was mortified.. it was a different world back them. My parents made me feel ashamed because it was "unnatural" I am sure glad times have changed!

Title: Re: What was the first item you wore and at what age?
Post by: randim on January 21, 2020, 09:34:48 am

I'm pretty sure it was my Mom's girdle and stockings.  I can't remember how young, but pretty young.  Certainly no later than early elementary school.

Title: Re: What was the first item you wore and at what age?
Post by: Chris71 on January 21, 2020, 11:28:33 am

I was around 44 or 45 the first time I tried on a pair of womens panties.

I guess I'm not "normal" in that I never tried on my mother's clothes.  Didn't have any sisters.   I just never had the desire until I was in my early 40's and had been dating my wife for about a year.  We lived 80 miles apart when we met.  I would drive to her city on Friday after work and stay the weekend with her.  Then drive back to work Monday morning.   She came to my place a few times but she has 2 dogs and I lived in an apartment at the time so it made it really inconvenient for the dogs.

After one of her weekend visits to my apartment, I discovered a pair of purple satin panties in the dirty clothes bin.  I didn't think anything of it, and tossed them into the washer with some of my purple shirts and dark colors.  I put them in the dryer, still not having any thoughts of putting them on.   As I was taking the clothes out of the dryer and hanging my shirts, the panties tumbled out and landed at my feet.  That's when it started.

I picked up the purple satin panties and hooked my thumbs into the waste band and held them up to myself.  Hmmmmmmmm, pretty small..... not sure if I should do this..... probably won't even fit.  Meh, worth a shot.  I squeezed and wriggled into them. Snapped a pic with my cell phone and then txt'd it to her.

That's all it took.  She immediately responded back with adoration and suggested we go shopping the next weekend.  I was taken back.  I did not expect her to react that way and certainly wasn't ready to "go girl shopping" as she had phrased it.  She spent over $300 buying lingerie, shoes and clothes for me that weekend.  I was excited but also quite scared.   Where was this going?  What have I started?  Is she REALLY that turned on by this?

That was about 4yrs ago.  She asked me to marry her in 2017 and I accepted her proposal immediately.   

I wear panties 24/7 now.  Still wear regular cis male clothes to work and in public, but I'm always wearing panties underneath.  When it's cold outside, I will occasionally wear a bra because I can put on a t-shirt and a sweater over the top so nobody sees the straps.  I dress at home a few nights a week.  I get home from work before my wife and she will often send a txt and ask me to put on a specific dress or pair of heels to cook dinner in.  She gets a thrill from coming home to find me in the kitchen wearing heels and a dress, with some eye mascara and lipstick.

Title: Re: What was the first item you wore and at what age?
Post by: Chris71 on January 21, 2020, 12:03:52 pm

Curious how you pulled that off. Most of the panties my wife buys for me have those anti-theft devices attached. 

Title: Re: What was the first item you wore and at what age?
Post by: JennyTG on January 21, 2020, 01:42:43 pm

Quote from: Heather N on January 21, 2020, 09:27:03 am

for me , it was Halloween in 6th grade. My mom dressed me up and I did it several times after that, as I grew a bit older I would snag some of my sisters clothes as she outgrew them. I got caught by my father and I was mortified.. it was a different world back them. My parents made me feel ashamed because it was "unnatural" I am sure glad times have changed!

It certainly was a different world back then.  I had the same thing with my Mom when she caught me back in the mid 80s.  Somehow I talked her out of going to a shrink and tried to explain it was a one-off exploration etc but really she knew how unlikely it would be to stop and had her suspicions/knowing glances from then on.  Thankfully she also kept it from my Dad, I think it would've been a different story otherwise.  Over the time I also got religion to add to the guilt, it has been many years of unhappiness, conflict and numerous purges.  I'm so glad I've come out to the other side and recovered.  Of course forums like this have helped immensely as well.

~Jenny~

Title: Re: What was the first item you wore and at what age?
Post by: Rachel Montgomery on January 21, 2020, 03:36:57 pm

I don't know.  Probably my grandmothers fur lined bedroom slippers.  They were so feminine and soft and fuzzy that I couldn't resist.

Or, maybe it was a skirt suit of my mothers and some calf high boots, all of which would have been laughably too big at the time.   I remember having my sisters stand guard to tell me if anyone came our way, so I am guessing I had been caught wearing something else and either embarrassed or scolded.  All of this would have been before I was 5. 

By the time I was 6, I was borrowing (stealing and returning) my sister's clothes from her closet.  By that time, I no longer had my sisters stand watch, because I was hiding this from them too.  I'm not sure what happened to change things, but around my 6th birthday my grandmother saw me wearing one of her dresses and told me I was a pervert and going to Hell if I didn't change.  Since then, I have gone to serious effort to hide when I CD.   I also insisted in getting Baptized (which obviously didn't make GD go away).

Title: Re: What was the first item you wore and at what age?
Post by: Rachel Montgomery on January 21, 2020, 03:52:34 pm

Quote from: jacquelynh on June 09, 2016, 06:02:02 am

A dress my mom made me try on,I was 7 or 8 years old when this happened.My mom thought I looked cute in it

That seems like it would be so wonderful to have happen.  My mother would not endorse such.

Title: Re: What was the first item you wore and at what age?
Post by: Allie Jayne on January 21, 2020, 08:49:10 pm

Quote from: Chris71 on January 21, 2020, 11:28:33 am

I was around 44 or 45 the first time I tried on a pair of womens panties.

I guess I'm not "normal" in that I never tried on my mother's clothes.  Didn't have any sisters.   I just never had the desire until I was in my early 40's and had been dating my wife for about a year.  We lived 80 miles apart when we met.  I would drive to her city on Friday after work and stay the weekend with her.  Then drive back to work Monday morning.   She came to my place a few times but she has 2 dogs and I lived in an apartment at the time so it made it really inconvenient for the dogs.

After one of her weekend visits to my apartment, I discovered a pair of purple satin panties in the dirty clothes bin.  I didn't think anything of it, and tossed them into the washer with some of my purple shirts and dark colors.  I put them in the dryer, still not having any thoughts of putting them on.   As I was taking the clothes out of the dryer and hanging my shirts, the panties tumbled out and landed at my feet.  That's when it started.

I picked up the purple satin panties and hooked my thumbs into the waste band and held them up to myself.  Hmmmmmmmm, pretty small..... not sure if I should do this..... probably won't even fit.  Meh, worth a shot.  I squeezed and wriggled into them. Snapped a pic with my cell phone and then txt'd it to her.

That's all it took.  She immediately responded back with adoration and suggested we go shopping the next weekend.  I was taken back.  I did not expect her to react that way and certainly wasn't ready to "go girl shopping" as she had phrased it.  She spent over $300 buying lingerie, shoes and clothes for me that weekend.  I was excited but also quite scared.   Where was this going?  What have I started?  Is she REALLY that turned on by this?

That was about 4yrs ago.  She asked me to marry her in 2017 and I accepted her proposal immediately.   

I wear panties 24/7 now.  Still wear regular cis male clothes to work and in public, but I'm always wearing panties underneath.  When it's cold outside, I will occasionally wear a bra because I can put on a t-shirt and a sweater over the top so nobody sees the straps.  I dress at home a few nights a week.  I get home from work before my wife and she will often send a txt and ask me to put on a specific dress or pair of heels to cook dinner in.  She gets a thrill from coming home to find me in the kitchen wearing heels and a dress, with some eye mascara and lipstick.

Chris, you have described so many peoples dreams on here! We all dream of having an enthusiastically supportive partner, so I hope you realise how lucky you are.

Hugs,

Allie

Title: Re: What was the first item you wore and at what age?
Post by: Chris71 on January 22, 2020, 02:06:59 pm

Quote from: Allie Jayne on January 21, 2020, 08:49:10 pm

Chris, you have described so many peoples dreams on here! We all dream of having an enthusiastically supportive partner, so I hope you realise how lucky you are.

Hugs,

Allie

Oh believe me, I know exactly how lucky I am.  I've managed to capture the attention and adoration of a lovely woman.  She's my best friend.   The sex and the kinky fun is just one aspect of our relationship.   We've never had a fight.  We keep each others secrets. We do everything together.

Title: Re: What was the first item you wore and at what age?
Post by: NicoleClio on February 07, 2020, 11:12:49 am

We had a “rag bag” which was kept in the bathroom. My mother put old clothes in there and I tried them on from an early age. It was always secret and I always felt guilty afterwards. My favourite was a big blue 50’s style skirt which I loved. Sadly one day my dad tore it up to make rags to clean the car.

Title: Re: What was the first item you wore and at what age?
Post by: JennyTG on February 07, 2020, 01:56:55 pm

Quote from: NicoleClio on February 07, 2020, 11:12:49 am

We had a “rag bag” which was kept in the bathroom. My mother put old clothes in there and I tried them on from an early age. It was always secret and I always felt guilty afterwards. My favourite was a big blue 50’s style skirt which I loved. Sadly one day my dad tore it up to make rags to clean the car.

Geeez, that must've broke your heart :(

~Jenny~

Title: Re: What was the first item you wore and at what age?
Post by: Susan R on February 07, 2020, 03:13:05 pm

I didn’t dress myself as female in the beginning. My two older sisters dressed me up at age 4. When they were out with their friends, I would go back and continue to put on the same clothes they had put on me earlier.  The exact article of clothing I put on without help is hard for me to recall.  I’m pretty sure it was a pair of panties as it would've been the obvious first item to put on myself.  Sadly, this all came to an abrupt stop after my mother caught me in their room alone one afternoon wearing one of their outfits.

Susan R🌷

Title: Re: What was the first item you wore and at what age?
Post by: sarahc on February 07, 2020, 03:44:58 pm

I have no idea what it was I wore or when, but it was sometime around 8-10 years old. There could have been an incident when I was younger, but somewhere around 10 years old was when it got more frequent.

Sarah

Title: Re: What was the first item you wore and at what age?
Post by: Heather A on February 07, 2020, 08:20:19 pm

Its hard for me to remember exactly but I would say when I was 11 or 12, my parents just purchased a new house and lucky me I got to live in a room that used to belong to a girl.  I only new this because she left one of her silk skirts in the closet on a shelf.  I honestly don't know if they have a actual name.  I wore that a few times but I had to be discreet since I knew my parents would not understand.

Sadly my mother one day found my hidden gem and I blamed I don't know where it came from it must have always been there.  Luckily this was true for me so she believed me but I still ended up getting in trouble but I don't remember exactly what punishment I got.  It was a few years before I worked up the courage to wear any female clothing after that.  I would have loved to have had sisters to borrow clothing from growing up, but I was not so fortunate.

Title: Re: What was the first item you wore and at what age?
Post by: NicoleClio on February 08, 2020, 10:13:04 am

Quote from: JennyTG on February 07, 2020, 01:56:55 pm

Geeez, that must've broke your heart :(

~Jenny~

I’ve been looking for one like it ever since

Title: Re: What was the first item you wore and at what age?
Post by: JennyTG on February 08, 2020, 04:21:35 pm

Quote from: NicoleClio on February 08, 2020, 10:13:04 am

I’ve been looking for one like it ever since

If that was me I think I would've taken it out of that rag-bag pronto and hidden it well, esp that young when clothing is precious!  Too bad if I was found out.  I remember when I was young there was a bag of goodies for goodwill (mainly for sis and mum) that stayed around for a long time.  When that eventually disappeared I probably cried a bit, lol.

~Jenny~

Title: Re: What was the first item you wore and at what age?
Post by: NicoleClio on February 12, 2020, 10:52:23 am

I wish I had but I was very young and also had to share a room with my older brother.

Title: Re: What was the first item you wore and at what age?
Post by: Dayle1957 on February 12, 2020, 11:27:24 am

When I was about 9 or 10 I began wearing my mom's baby-doll nighties whenever I could get the chance.  Usually for just a few minutes at a time.  I would wait until nobody was upstairs, sneak into my mom and dad's room, put on the baby-doll, run into my bathroom to look at myself, then very quickly put it all back.

When nobody was home I would run around the house and sometimes go in the backyard with it on.

I never felt more free in my entire life.

Title: Re: What was the first item you wore and at what age?
Post by: JennyTG on February 12, 2020, 05:43:32 pm

Quote from: Dayle1957 on February 12, 2020, 11:27:24 am

When I was about 9 or 10 I began wearing my mom's baby-doll nighties whenever I could get the chance.  Usually for just a few minutes at a time.  I would wait until nobody was upstairs, sneak into my mom and dad's room, put on the baby-doll, run into my bathroom to look at myself, then very quickly put it all back.

When nobody was home I would run around the house and sometimes go in the backyard with it on.

I never felt more free in my entire life.

Sounds familiar...but if I went outside I think my heart would've stopped, you brave thing.

~Jenny~

Title: Re: What was the first item you wore and at what age?
Post by: SarahEL on February 12, 2020, 06:25:20 pm

I grew up in the 80's - the era of Olivia Newton-John, exercise videos and aerobics. My mom had a pink leotard, with leggings and ankle warmers. As far as I can remember, that was the first thing I wore. I did used to also sneak underskirts (slips) and pull them on too and swirls and swish around in them (all in secret of course.)
I found a picture of what it looked like -  (its not me, obvs.)
(https://fashiondiiary.com/wp-content/uploads/2019/05/Best-80s-Fashion-Look-1980s-aerobics-fashion-yes.jpg)

I was a stylish 10 year old! :)

Title: Re: What was the first item you wore and at what age?
Post by: madeleine on February 12, 2020, 07:09:58 pm

When I was little, like six maybe?  I wrapped a piece of tuule around me.  This was in front of other boys and it was in a big bush in the front yard.  I wonder what they thought!

The first piece of clothing was in my teens and it was certainly panties and/or a bra - what power they had for/over me!  And they were my mother's  :embarrassed: and in secret.  I did this for a while with clothing and some makeup too.  I feel there was no way she couldn't have known.

Title: Re: What was the first item you wore and at what age?
Post by: JennyTG on February 12, 2020, 07:35:05 pm

Quote from: SarahEL on February 12, 2020, 06:25:20 pm

I grew up in the 80's - the era of Olivia Newton-John, exercise videos and aerobics. My mom had a pink leotard, with leggings and ankle warmers. As far as I can remember, that was the first thing I wore. I did used to also sneak underskirts (slips) and pull them on too and swirls and swish around in them (all in secret of course.)
I found a picture of what it looked like -  (its not me, obvs.)
(https://fashiondiiary.com/wp-content/uploads/2019/05/Best-80s-Fashion-Look-1980s-aerobics-fashion-yes.jpg)

I was a stylish 10 year old! :)

What a beautiful pic, thanks Sarah!  Yep, leotards and leg warmers were very popular in my teens, I saw them everywhere!  Never owned one though. 

Who hasn't swished and swirled in a slip before I ask you :)

~Jenny~

Title: Re: What was the first item you wore and at what age?
Post by: madeleine on February 12, 2020, 07:37:23 pm

Quote from: JennyTG on February 12, 2020, 07:35:05 pm

Who hasn't swished and swirled in a slip before I ask you :)

~Jenny~

BIG smile for that!

Title: Re: What was the first item you wore and at what age?
Post by: JennyTG on February 12, 2020, 07:45:32 pm

Quote from: madeleine on February 12, 2020, 07:09:58 pm

The first piece of clothing was in my teens and it was certainly panties and/or a bra - what power they had for/over me!  And they were my mother's  :embarrassed: and in secret.  I did this for a while with clothing and some makeup too.  I feel there was no way she couldn't have known.

I think for the most part no matter how carefully you put stuff back they know.  I was caught with a surprise pop-in from her work in the middle of the day, it was quite an afternoon :o  All I'm happy about is my Dad wasn't told, heaven knows what would've happened.

~Jenny~

Title: Re: What was the first item you wore and at what age?
Post by: JennyTG on February 12, 2020, 07:55:49 pm

Quote from: NicoleClio on February 12, 2020, 10:52:23 am

I wish I had but I was very young and also had to share a room with my older brother.

OIC, that could be tricky :-\

~Jenny~

Title: Re: What was the first item you wore and at what age?
Post by: JaimeL71 on February 13, 2020, 09:14:35 am

Quote from: SarahEL on February 12, 2020, 06:25:20 pm

I grew up in the 80's - the era of Olivia Newton-John, exercise videos and aerobics. My mom had a pink leotard, with leggings and ankle warmers. As far as I can remember, that was the first thing I wore. I did used to also sneak underskirts (slips) and pull them on too and swirls and swish around in them (all in secret of course.)
I found a picture of what it looked like -  (its not me, obvs.)
(https://fashiondiiary.com/wp-content/uploads/2019/05/Best-80s-Fashion-Look-1980s-aerobics-fashion-yes.jpg)

I was a stylish 10 year old! :)

Love it!

As I said earlier, I too was a child of the 80s and this type of clothing was some of my first forays into CD'ing.  To this day, I have a large assortment of women's leggings and workout tops, but I do miss the workout clothes of the 80s.

My sister had this set (although the leotard was pewter and pink) that I used to slide into when she wasn't home:
(https://i.imgur.com/YSmDm5f.jpg)

Title: Re: What was the first item you wore and at what age?
Post by: Dayle1957 on February 13, 2020, 10:12:39 am

I think my mom knew. She would leave undergarments in places I could easily find them such as a girdle under the sink in our guest bathroom. I’d have to “go to the bathroom” about 20 times a day!!  Once, when I was out of HS I left a nightie and panties in my bedding when I was in a hurry to leave the house in the morning. Well, my mom chose that day to wash my bedding!  When I came home the nightie and panties were neatly folded and sitting on the drier. They stayed their untouched for several days before I had the courage to retrieve them.
All kind of weird I know.
I think she knew of my desire to be a girl, and at some level wanted to help but in those days it just couldn’t be addressed out loud.
Now days she might have asked me about it and been an ally.
I so wish I could have gone on Andro-blockers before puberty and transitioned in my late teens or twenties!!

Title: Re: What was the first item you wore and at what age?
Post by: JennyTG on February 13, 2020, 01:14:16 pm

Quote from: Dayle1957 on February 13, 2020, 10:12:39 am

I think she knew of my desire to be a girl, and at some level wanted to help but in those days it just couldn’t be addressed out loud.
Now days she might have asked me about it and been an ally.

I know what you mean, same situation.  When sprung it did go from shock and shrink talk to gradual acceptance, teasing and knowing glances when stuff wasn't put back exactly.  That's as far as it went.  She was definitely knowledgeable about CDing never going away (for 99%).  Of course I lied at the time and said it was just a one-off experiment.  It's nice to think she would've jumped on board eventually, not so sure though.

~Jenny~

Title: Re: What was the first item you wore and at what age?
Post by: FrenchieVanina on February 14, 2020, 04:07:22 am

I was 6 yo, mid 70's era. Wore some mom's stuff : lacy satined panties, so soft and a bit cold on the skin, suntan pantyhose, and an all-in-one, with hooks and a zipper...
I wished I had a sister, but dressed since then in mom's clothes, as long as I was young and petite enough to do. At a time even her shoes were fitting perfectly, and I spent hours fully dressed (from bra to dress), with jewellery on, pretending I was a young woman...

Title: Re: What was the first item you wore and at what age?
Post by: Dayle1957 on February 14, 2020, 11:52:49 am

It sounds wonderful.  Such precious memories.

I've only fully dressed a dozen or so times in my life in truly feminine attire.  I've gone out many times in jeans and panties and such, which is nice of course, but not quite the same.

Thanks for sharing this!

Title: Re: What was the first item you wore and at what age?
Post by: KateWelleck on May 30, 2020, 01:45:47 pm

Bra and panties at around 16 or 17
Haven't stopped since

Title: Re: What was the first item you wore and at what age?
Post by: Ellie_Arroway on May 30, 2020, 02:09:06 pm

Probably a nappy at age 0, but I can't remember...

Title: Re: What was the first item you wore and at what age?
Post by: gail123 on June 07, 2020, 06:57:24 pm

Panty hose.

Around 12 or 13.

Still get excited putting them on, even after 60 years.

Title: Re: What was the first item you wore and at what age?
Post by: FlatsLover92 on June 08, 2020, 04:13:18 pm

A pair of flats i bought my self in person, around 16 back in 2008. I  said they were not for me haha
Now i have many shoes( flats, heels, sandals) started wearing flats in public since end if March. Now i own other female items. One item at a time in public until it becomes normal.

Title: Re: What was the first item you wore and at what age?
Post by: JennyTG on June 09, 2020, 02:57:37 am

Quote from: FlatsLover92 on June 08, 2020, 04:13:18 pm

A pair of flats i bought my self in person, around 16 back in 2008. I  said they were not for me haha
Now i have many shoes( flats, heels, sandals) started wearing flats in public since end if March. Now i own other female items. One item at a time in public until it becomes normal.

Sorry ott but I did once wear pink ballet flats into a crowded shopping mall, fun times.  I certainly could walk faster in them than my 4" boot heels :D  I never really took to them again, I think they were purged a good many years ago.  I have acquired many open toe sandles and boots with a decent heel on them.  They always complete my femme wardobe when out in public, not so much flats currently though :)

~Jenny~

Title: Re: What was the first item you wore and at what age?
Post by: Zoe_Kay on June 23, 2020, 09:53:51 pm

A ballet tutu dress, age 7

Title: Re: What was the first item you wore and at what age?
Post by: Dweia on June 25, 2020, 08:01:52 am

When I was 7, I needed skates for the school.
So........ what happened that as Christmas present I received women figure skates.
When I realized that I was forced to use those, I was embarrassed at school.

I think it was round 12-13 when I was trying on my sister clothes.
At age 15 I went to nearest city to buy my first bra and panties.

Title: Re: What was the first item you wore and at what age?
Post by: lucysarah on July 08, 2020, 04:18:53 pm

It was my sisters polka dot skirt about 6 years old, my mum caught me.

Title: Re: What was the first item you wore and at what age?
Post by: Northern Star Girl on July 08, 2020, 07:11:35 pm

Quote from: lucysarah on July 08, 2020, 04:18:53 pm

It was my sisters polka dot skirt about 6 years old, my mum caught me.

@lucysarah   
Dear Lucy
    Please know that I am not trying to hijack your post but first I wish to Officially Welcome YOU to Susan's Place.
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    I want to warmly WELCOME you to Susan's Place. 
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    Please come in and continue to be involved at your own pace.   Other members will be along shortly to give you their thoughts about your questions and concerns that you mentioned in your very first posting.
   
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Please look closely at the LINKS in RED, answers are there to many questions that new members ask....

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Title: Re: What was the first item you wore and at what age?
Post by: Northern Star Girl on July 08, 2020, 07:11:47 pm

@lucysarah
Dear Lucy:

OH, and another thing....
If you feel so inclined please feel free to stop by the Introductions Forum (https://www.susans.org/forums/index.php/board,8.0.html) to tell more members about yourself!
 
With more exposure to more members here you will be able to get more responses to your questions and concerns.

Wishing your well as you continue to be involved in the forums.

NOTE: Now, after all of this Greeting and Welcoming stuff, I will give you and other readers the thread back so that the conversation can continue

Again, Welcome to Susan's Place.
Danielle

Title: Re: What was the first item you wore and at what age?
Post by: Ciara on July 09, 2020, 04:33:13 am

My sister's pleated skirt, bra and panties. I'm not sure exactly what age but I was certainly under 10. I can still picture them. The bra clips were at the front.........what a great idea 🙂.

Title: Re: What was the first item you wore and at what age?
Post by: MxRileyQuinn on July 09, 2020, 11:04:39 am

I'm from a rather large family (mom, dad, three brothers, and one sister) so there was always a LOT of laundry to be done.  Chores were on a rotating schedule, and though I HATED folding and putting away clothes for the most part, "laundry week" gave me a great opportunity to try on (in secret) my mother's or my sister's clothing.  My mother's clothes were too big for quite a while and my sister's were too small, but that eventually evened out.  I'd try on all varieties of their clothes, and I cannot remember a specific first outfit, though I do have very specific memories of trying on her panties and bra so perhaps that was it.  I do remember that it was my mother's clothing I tried first as my sister's were far too small to try on at the time (and I felt guilty enough trying on my mom's clothes).  I was about ten when I first started all that.

Title: Re: What was the first item you wore and at what age?
Post by: Dayle1957 on July 14, 2020, 02:46:49 pm

These are some of the most wonderful memories I have.  I cannot forget the absolute euphoria of pulling up the panties, and feeling the silky soft baby-doll top as I put it over my head and it hung so gently on my shoulders.

That was the closest I ever felt to being truly ME.  Especially when I was still prepubescent and had not had to go through the torture of male puberty.

Title: Re: What was the first item you wore and at what age?
Post by: barbie on July 14, 2020, 04:36:31 pm

It was silk stockings at age 4-5, which were of a young lady visiting and staying at my house. As I remember, the color was blue. I was strangely attracted to them, and tried to wear when I was awaken at the midnight. They were too big and loose to fit my tiny legs, which I did not expect. I was disappointed.

Nowadays I usually wear stockings only in winter. I am thinking of wearing blue ones this summer.

(https://live.staticflickr.com/65535/48989803146_8d18772e25_b.jpg)

barbie~~

Title: Re: What was the first item you wore and at what age?
Post by: Liv_J on July 19, 2020, 09:23:22 am

Quote from: Allison Wunderland on July 21, 2015, 01:19:21 pm

Bath towels as skirts, about 4 yrs. old. And so, is it trans, cross, ambiguous, or sometimes a towel is simply a towel, to paraphrase Freud.

 :D I wrapped a towel round my waist and one round my head, when I was about 9 or something, to try to feel/look girly, and my little brother, who would have been about 7, said 'you look exactly like a member of the opposite sex'  :laugh: :laugh:  He could come out with some funny things sometimes...

First time when I was about 3 or 4 maybe? There is an old photo in an album of my in a silk night gown and a hat belonging to my mum, and I look a little bit serious and wistful as though already slightly worried that I like this but I'm not sure boys are supposed to do it :-/ 

Title: Re: What was the first item you wore and at what age?
Post by: C-Woo on July 20, 2020, 01:33:00 pm

A pink diaper when I was about 4? As far as clothes go it was panties when I was 12ish

Title: Re: What was the first item you wore and at what age?
Post by: Denise K on July 26, 2020, 09:25:28 pm

It was my mom's tan pantyhose when I was around 9. I had started buying them for myself at 12 and I remember the fear to find a safe place for hiding them at home.

I am still a collector of all shades of pantyhoses and  I have that urge to put them on under my skirts even in hot summers, and that is not a good idea. :)

But well, it is hard to resist

Title: Re: What was the first item you wore and at what age?
Post by: MelissaCD on August 01, 2020, 10:50:14 am

Girlfriends panties and skirt when I was 18.

Title: Re: What was the first item you wore and at what age?
Post by: amymichelleb73 on September 14, 2020, 05:49:09 pm

Probably around 7 as I slightly remember think it was my mom's knee highs.

Title: Re: What was the first item you wore and at what age?
Post by: CaelaNotKayla on September 15, 2020, 02:07:36 am

Mine was a red dress of my moms, and one of her wigs when I was about 4. I got to wear them around the house- and even to school for the Halloween party!

Caela

Title: Re: What was the first item you wore and at what age?
Post by: TSL_NB on September 18, 2020, 10:39:32 am

When I was about four years old, I remember looking into my mom's makeup mirror.

I was absolutely enamored by it.  I loved how the lights on the mirror reflected on my iris (making that little halo within the iris), and I remember using her lash curlers, and then I tried a bit of her blue eyeshadow, and I just lit up with giddiness (which can happen when you're that young, too).

So yeah, it wasn't an article of clothing, but that would be my first 'item'...the eyeshadow. :)