THE OFFICIAL: What were the first items you wore?

Every story begins somewhere, so tell us how you got started crossdressing. Only one (1) topic per member, please!

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DebbieW
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Re: THE OFFICIAL: What were the first items you wore?

Post by DebbieW »

My first item of female clothing was tights. Going back more years than I care to remember I remember when in the bathroom I looked into the laundry basket and found a pair of my Mother's smokey grey sheer tights and put them on and it felt great. Coming forward many years things graduated to skirts.
Sandy K.
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Re: THE OFFICIAL: What were the first items you wore?

Post by Sandy K. »

The first i remember is panties and still my favorite.
MichelleZ
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Re: THE OFFICIAL: What were the first items you wore?

Post by MichelleZ »

I started collecting my mother's nylon stockings out of her bedroom waste basket. Wore them in bed with rubberbands to keep them up. She figured it out somehow and would tell it's time to empty her trash and sure enough, there would be a stocking or two in there. Later on when pantyhose became popular she started buying me new NoNonsense pantyhose and would stash them for me in the usual spot. I miss her.
Rose N.
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Re: THE OFFICIAL: What were the first items you wore?

Post by Rose N. »

First items!
Knickers/panties. No, not Mums (& I didn't have sister). I'd not even thought of using anyone else's underwear as I'd had quite enough of wearing hand me downs and things which extended family thought was OK for me, as it was.

I plucked up enough courage to buy some of my own. Amazing, really, seeing as how shy a youngster I was. :oops:

Brief/bikini type sheer net knickers with hearts outlined in red all the way over. Makes my heart speed up even now. @@9@@

I suppose I'd better write a story for the "how it began" thread.
Straight crossdresser - A man in a skirt, really!
I just love the freedom.
Mike P.
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Re: THE OFFICIAL: What were the first items you wore?

Post by Mike P. »

I used to wear my mothers's bathing suit, one piece. I liked the way it felt, smooth and it was tight, black.
"Let your heart sing loudly!"
Bobby T.
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Re: THE OFFICIAL: What were the first items you wore?

Post by Bobby T. »

they have pictures of me in my sisters crineoline when i was 1 but started wearing my sisters dresses when i was 9
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AJ West
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Re: THE OFFICIAL: What were the first items you wore?

Post by AJ West »

I was about 4 or 5 and mom's stockings were in the laundry room and I love their feel on my legs. I progressed from stockings and garters (they were hard to figure out back then) to pantyhose, shoes, more shoes, mores shoes, then added slips and then a bra. I was older before I started completely dressing completely with wig, make-up etc.
Not sure where I'm going, but there's no since being late
Allie Nichole
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Re: THE OFFICIAL: What were the first items you wore?

Post by Allie Nichole »

i was about just a toddler still in diapers acording to my mom, and i would put on her jewlery and try to wear her shoes. than when i was three i remember actually doing that stuff.


From there it went on to nylons, and when i was older (12 ish?) i would wear her bras when i had a chance to. first time i was fully dressed head to toe with makeup and wig was Dec. 14 2012. so i have that as my "Birthday" in adition to my real birthday dec. 14 is the day allison was fully realised as who i truly am.
To be sane is to be normal,
To be normal is to be avarage,
To be avarage is to be Mediocre,
-I never thought mediocricy was worth striving for!
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Rhanda
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Re: THE OFFICIAL: What were the first items you wore?

Post by Rhanda »

I was invited to a Halloween party when I was in the fifth grade and knew that both boys and girls were invited. I begged my sister who is three years older to let me wear an outfit that she had outgrown. by that time she had started to wear makeup and she suggested that I also wear some of that. What a charge. Her old Mary Jane shoes were just my size. The only Eye makeup commonly used by school girls at that time was cake maskara that as applied with a little brush using water to activate. I had the whole works plus a wig and a loosly fitting eye mask. I spent the whole evening getting attention from my school buddies who didn't reccognize me.
I have loved wearing womens underware daily all of my adult life and my sweet wife has willingly done my hand laundry. She has never made a big thing of it.
There is much more but you will have to wait

Thanks for the memories,
Rhanda
Carla Michelle
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Re: THE OFFICIAL: What were the first items you wore?

Post by Carla Michelle »

As early as I can remember I was in mothers panty drawer. Dressing up continued off and on and continues now. More of an everyday thing now than before and more accepting of myself this way.
~Carla Michelle a.k.a. Mickey~
Steffi Lynn
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Re: THE OFFICIAL: What were the first items you wore?

Post by Steffi Lynn »

When I was about 5 or 6, I used to sneak into my older Sisters room and try on her dresses. I loved the way they felt, and how pretty I looked in them. It wasn't until I was a few years older that I had the opportunity to raid Mom's bras and panties!
Moira
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Re: THE OFFICIAL: What were the first items you wore?

Post by Moira »

My first recollection was when I was about 13. My mother used to take in laundry for some university co-ed's and the laundry room was right next to my bedroom so I would sneak out at night and rummage through the laundry hamper and then wear a pair overnight and return them to the hamper the next morning before anyone noticed.
Martina Hall
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Re: THE OFFICIAL: What were the first items you wore?

Post by Martina Hall »

I'm sure it was pantyhose, around age 10. Then, when in ninth grade, our high school band and drama departments put on a musical, and everyone had to wear liner, mascara, etc. or you look awful under the bright stage lights. A couple of the guys continued to wear mascara after our last performance, which gave me some hope for the future of the human race.
Wonder if any of those men still dress up. Probably more than any of us would suspect. For each of us, there may be a dozen who never tell ANYONE.
I AM my own hot girlfriend.
Jen S.
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Re: THE OFFICIAL: What were the first items you wore?

Post by Jen S. »

I was probably 7 and it was a pink and white checkered pattern ankle length nightgown that belonged to my mom. Too young to be embarrased, I marched right out to the living room so my mother, grandmother and aunt could see me. They fawned over me for a few minutes and decided that a wig was needed which they quickly retrieved and fastened to my head. A tiny spritz of perfume and I was put to bed as a girl for the first time. I'd love to live that night all over again.
TammyT
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Re: THE OFFICIAL: What were the first items you wore?

Post by TammyT »

I remember being intrigued by the fabrics and softness of my mum's and aunt's dresses when I was as young as about 8, though they were just episodic interests up until after I started high school. To this day, I don't know why I went from being intrigued to feeling the urge to try something on. I would have been about 14-15 before I first tried any women's clothes on -- just outerwear and padded bras, never panties. From there, there were many secret dress-up sessions when there was no one else at home. I was always petrified of doing anything while dressed up, though, and because I was always alone, I never really wanted to do anything. My mum and I are still the same dress size, but I've long outgrown her shoes. (I reckon I share her love of shoes and fashion more than my sister!) I've eased up on raiding her wardrobe though, partly because she still doesn't know, but mainly because I would take everything off as soon as I put it on.
Very happy being a guy, but I also love fashion. We are all valued, and my feminine side is just one facet of the gem as a whole.
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