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The power of the past

29 Posts
13 Users
74 Reactions
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Posts: 953
Lady
Topic starter
(@maureen76)
Noble Member     Bay Area, California, United States of America
Joined: 7 months ago

I think many of us here understand the power of our first time doing something new and "exciting". Such as our first kiss, the first time behind the wheel of a car, etc.. So, it is with our first experience with women's clothing. From my personal memories, and also hearing from so many of you, it seems we can remember that moment with incredible clarity. While so many memories gradually fade and blend in to one another, our first time remains clear and sharp. Also, it seems the majority of us started by going through our mothers or sisters dresser drawer and being amazed at the "strange, exotic, and alluring" underwear they wore compared to our plain cotton briefs. What mysterious creatures that were allowed to dress in such
"impractical clothing". How could we not become hooked?

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8 Replies
 Erin
Princess
(@erinb)
Joined: 5 months ago

Noble Member     Ohio, United States of America
Posts: 1150

@maureen76 I do remember sneaking panties and dresses from my older sister mom use to do garage sales ever year I would sneak peek and hide things away to wear later on late nights still today ever wonder if I was caught I was never questioned tho still a mystery in my mind today 

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Lady
(@maureen76)
Joined: 7 months ago

Noble Member     Bay Area, California, United States of America
Posts: 953

@erinb what a sneaky little girl you were---of course you weren't stealing just re-purposing the items---Hugs, Maureen

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Duchess
(@rebeccaoh)
Joined: 7 months ago

Estimable Member     Oxford, Ohio, United States of America
Posts: 75

@maureen76 I know I dressed up alone first for sure, but one of the most memorable was with an ex as a teenager. We were maybe 15 years old, and we had some alone time in her families basement. We were watching a movie and she had always been a sort of playful/unusual girl and had started teasing me to please put in some of her clothes. She had no idea of course about my private dressing that I did. Also, before this she had bet me something that I lost and had to shave my legs. Putting the pieces together after so many years, it’s pretty obvious that she had some interests in some gender bending, and why I was so willing to “play along”. When I dressed up for her it was very simple, just a denim short skirt and a hollister top I believe. Definitely a high school preppy look which I always liked. We had some quick high school kissing in the outfit that I am willing to share. Always will be a great memory for me, and also kind of sad I never came clean to her about how much I loved it obviously…

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Lady
(@maureen76)
Joined: 7 months ago

Noble Member     Bay Area, California, United States of America
Posts: 953

@rebeccaoh Great story Rebecca!---

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(@slingback542)
Joined: 3 months ago

Eminent Member     Tyne and Wear, United Kingdom
Posts: 10

@maureen76 

My sisters were to blame for me, they were 8 and 9 when I was born,  I was there live action barbie doll.

They got older and stopped,  I got older and carried on.

During a very low part of my life, around 5 years ago,  I had a partial break up with my darling wife. 

I confessed to my sister about this other part of me, she was cool. Thanks to her we are still together and have boundaries which I try my best to adhere to. 

Yep I'm on my last chance. 💔💔💋

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Lady
(@maureen76)
Joined: 7 months ago

Noble Member     Bay Area, California, United States of America
Posts: 953

@slingback542 Good luck---hang in there

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Duchess
(@mkat3874)
Joined: 4 months ago

Reputable Member     Northeast GA , Georgia, United States of America
Posts: 167

@maureen76 

Funny, but I simply don't specifically remember the first time. I do recall being about 8 yrs old and trying on some stockings that belonged to my mother but the details of the exact moment escape me. I never had any sisters to borrow from. I was a typical GenX kid whose parents both worked long hours away from home so I had the house all to myself for 3-4 hours every day from about 11 yrs old onward.  By that age I had started trying on some of her dresses and shoes but didn't go any further until years later after marrying.  

 

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Lady
(@maureen76)
Joined: 7 months ago

Noble Member     Bay Area, California, United States of America
Posts: 953

@mkat3874 even though I remember the first time very clearly---I know their were other times after that I barely remember or forgot---I think my desire ebbed and flowed depending upon what else was going on in my life

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Posts: 281
(@coloradog1)
Honorable Member     California, United States of America
Joined: 2 years ago

I really cannot remember the exact first time. But many early memories of trying on women’s clothes stick out in my mind

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1 Reply
Lady
(@maureen76)
Joined: 7 months ago

Noble Member     Bay Area, California, United States of America
Posts: 953

@coloradog1 I think they do for most of us--good memories

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Posts: 1109
Duchess Annual
(@firefly)
Noble Member     Panama, Panama, Panama
Joined: 7 years ago

First times are precious, Maureen.

Sometimes I think I clearly remember my first women's piece, and it seems to me that it was a one-piece bathing suit. I am almost sure. But other times, I get a confusing mix of memories. Perhaps I can paraphrase a poem by Edgar Allan Poe:

It was many and many a year ago,

In a country by the sea,

That a maiden there lived whom you may know

By the name of Gisela Claudine.

Happy Woman Face

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Posts: 2095
Hostess
(@cdsue)
Famed Member     Delaware, United States of America
Joined: 5 years ago

Maureen -

The memories of firsts - what an interesting topic.

As I remember my first dressing experience: it was after school, home alone I went into my parents room. I looked in my mother's lingerie drawer and took out a pair of black lace trimmed panties, a matching bra, garter belt and stockings. I put them on and posed in front of the mirror. I took it all off and pout it back where I found it. I would dress a couple days a week when home alone. I slowly added a dress. That lasted for about a year, the risk of getting caught became too high so I stopped. 

XOXO
Suzanne

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5 Replies
Lady
(@maureen76)
Joined: 7 months ago

Noble Member     Bay Area, California, United States of America
Posts: 953

@cdsue Suzanne----sounds familiar----did you have trouble with the garter belt and stockings the first time?

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Duchess
(@missylinda)
Joined: 2 years ago

Noble Member     Ft Worth, Texas, United States of America
Posts: 847

@maureen76 was so worried I would run the nylons , was extra careful .  Afterwards, careful to work on the tops so tabs impression did not show.  I was a sneaky little guiro🫣🤭🤗

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Lady
(@maureen76)
Joined: 7 months ago

Noble Member     Bay Area, California, United States of America
Posts: 953

@missylinda Yes you were---sneaky and careful at the same time---most wouldn't have thought about the tab impression

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Hostess
(@cdsue)
Joined: 5 years ago

Famed Member     Delaware, United States of America
Posts: 2095

@maureen76 not that I remember - that was (and still is) the fun part and oh so girly hooking stockings to garter belt tabs

XOXO
Suzanne

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Lady
(@maureen76)
Joined: 7 months ago

Noble Member     Bay Area, California, United States of America
Posts: 953

@cdsue amen to that sister

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Posts: 3402
Hostess
(@ab123)
Illustrious Member     Surrey, United Kingdom
Joined: 5 years ago

I had a memory where it was actually my mother who put me in a dress when she entered me in a fancy dress competition as 'Lady Muck', I was four! I remember the location and felt really nice walking about with the other girls I don't remember any boys entering. That started me off as I would wear my sisters clothes ad would be happy to dress as a girl for fun with the approval of the family. 

I often wondered if there was any photos of that event and my mother said there wasn't. Many years later after her passing while going through her effects grainy cuttings from local newspapers were found of this and other events where I dressed. So there is photographic evidence of my very first dressing experience.

 

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2 Replies
Lady
(@maureen76)
Joined: 7 months ago

Noble Member     Bay Area, California, United States of America
Posts: 953

@ab123 Very interesting story--- my mom kind of started me off as well---but lost interest and didn't enter me into any contest where pictures were taken---I am assuming you won, of course

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Hostess
(@ab123)
Joined: 5 years ago

Illustrious Member     Surrey, United Kingdom
Posts: 3402

@maureen76 My mother started me off as such but later in life when being told of my crossdressing she said she never knew or realised I was dressing. She thought I was entering in the spirit of the events.

Oh and yes I did win as I was the youngest and probably cutest there!

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Posts: 2165
 J J
Lady
(@jjandme)
Famed Member     California, United States of America
Joined: 5 years ago

Oh yes, we do remember our firsts, but the second and thirds, become fuzzy fast. 

One of the things that keeps me dressing is the challenge of new things. While I enjoyed my first time dressing as a pre-teen, I also enjoyed my first time buyi g a bra, or my first vra fitting, going out in public, shopping for a wig, getting a make over, etc, etc, etc. Unfortunately, after all these years there are not too many firsts left to be had, so I have settled into a pattern of just enjoying the moment. It goesback to my thread of the thrill not being gone, but just settling into a pleasent pattern.

I love new challenges, but at my age there are fewer options, at least for things I am capable of doing.

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3 Replies
Duchess
(@melaniew)
Joined: 1 month ago

Trusted Member     South Glamorgan, United Kingdom
Posts: 28

@jjandme wonderfully put. All those moments also feel to me like times when I took another wild, exciting leap into the unknown. My first time out for instance, I remember it so vividly and especially the unexpected sensation I had once I closed the hotel bedroom door behind me, of liberation, emancipation and nervousness ebbing away. 

I suppose that's also a function of it taking me so long to make these strides. The landmarks have often been far apart. I'm quickening my pace these days.

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Lady
(@maureen76)
Joined: 7 months ago

Noble Member     Bay Area, California, United States of America
Posts: 953

@melaniew not only our first experience is memorable but also all the other landmark moves as well---like the first time stepping out

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Lady
(@maureen76)
Joined: 7 months ago

Noble Member     Bay Area, California, United States of America
Posts: 953

@jjandme " after all these years there are not too many firsts left to be had, so I have settled into a pattern of just enjoying the moment."-----well said----we do change and a different type of pleasure takes over

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Posts: 2165
 J J
Lady
(@jjandme)
Famed Member     California, United States of America
Joined: 5 years ago

It is not a race, nor are there any prizes, other than self satisfaction. Some people are bold and like to push boundaries, both personal or societal, others are perfectly happy with the satus quo.

I just like doing new things and having new experiences, and dressing is just one of them. Many things I found fun, and glad I did them, and still may enjoy them, but they are not a priority for me. Others things have become a part of me and while I may not tick off new firsts, I still enjoy them. Dressing is one of them. I suspect I always will dress even though I am no longer push many new boundries for myself. To go back to my usual skiing analogy. While I am still dropping double diamond ski runs, my age and body no longer allow me to push the limits like I used to, and I am okay with that. Soon, I won't even be able to drop the challenging runs I can currently ski, and while I will miss it when it happens, I am content. I already passed that point in my rock climbing, and have had to scale way back my choices, but I have a wealth of memories of both rock climbing and skiing firsts, as I do with my dressing.

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Posts: 1778
Baroness
(@annaredhead)
Famed Member     Cornwall, United Kingdom
Joined: 11 months ago

My first time, I was 14 and had the house to myself. Random thought - what would it feel like to dress up like a girl?

So I borrowed one of my sister's bras, a pair of her knickers and a pair of her tights. Put them on, slipped a paid of rolled up socks into each bra cup and slipped on one of her dresses.

The bra and knickers were white, the tights were green, ribbed tights and the dress was one she had made. and was a beige colour A-line shape with a narrow waist.

I wandered round the house, stopped and looked at myself in different mirrors, I could feel the dress swishing on my legs, the draught. I had an hour, maybe not much more to safely had the house to myself but that hour has stuck with me.

This was nearly 40 years ago, it still feels like yesterday. 

 

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2 Replies
Lady
(@maureen76)
Joined: 7 months ago

Noble Member     Bay Area, California, United States of America
Posts: 953

@annaredhead you started much later than me----and you memory is much more vivid. But no matter the age or the exact circumstances the first time is always powerful

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Duchess
(@missylinda)
Joined: 2 years ago

Noble Member     Ft Worth, Texas, United States of America
Posts: 847

@annaredhead   Exactly like yesterday.  Still see myself dancing in front of the hall mirror in a lace panel girdle and nylons.  Biggest smile ever!

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