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My first time dressing

19 Posts
11 Users
107 Reactions
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Posts: 10
Lady
Topic starter
(@alana1955)
Eminent Member     Michigan, United States of America
Joined: 1 year ago

I had just turned 15 years old and my family was driving back from summer vacation out west. Somewhere in Nebraska on the interstate, we were behind a station wagon who had luggage on top, hooked to the rack. One of the suitcases fell off and my Dad had to make a sharp movement to miss it while it bounced in the middle of the road. The piece tumbled close to where we pulled off and my parents had me go get it instead of my younger sister. The address on the outside showed it belonged to a woman who lived about two hours from our house in Michigan.

Somehow when things were unpacked the suitcase ended up in my bedroom closet. Probably because mine was fairly empty compared to all the others. About 2 or 3 weeks later, I got home from the first week of school and my sister was still gone and my Parents were both working. Curiosity got the better of me and I pulled out the case and opened it.

It was a moment I will never forget...Women's clothes. There were 2 pair of slacks a few blouses and a Beige skirt. There was also several white silk panties, two white bra's and two packages of pantyhose. I just sat on my bed looking at the prize touching each item with almost a reverence. Time froze for me till I heard my sister entering the house. I put everything back quickly before she noticed. Over the next two weeks, everyday I would have to open that case and stare. Then came the day...September 21...There was just a half day at school and my parents told me to come home and stay there and not to go over to my friends house. I almost ran to my room and immediately went into my room and found the suitcase. Placing it on top of the bed, opened and spied the mini-skirt. Beige with a silk like lining that felt so good to the touch. Next thing and I remember it to this day..."How would it feel to wear it?" I swear that thought came out of nowhere. Quickly out of my pants, I put on the skirt and pulled the rear zipper up in place. The feeling of that silk and the edge of the skirt just above the knee was unlike anything I had felt before. All I could do was stand there in complete euphoria.

I had to walk around to feel the movement of this skirt on my legs. I think I was doing this for at least 30 minutes. Then looking again at the case I knew what was next. I took off my underpants and shirt. The panties were not the lacy or thong type. More like mine but silky and oh so soft. The bra was a bit difficult the first time. I took me a few moments to figure out to hook it in front the pull it around. The straps also was a bit difficult to keep straight. The blouse ended up being the one thing too large for me but I put it on anyway. After a few moments of just standing and taking in every feeling coursing through my veins. I ran to my mother's full length mirror and almost cried... I was beautiful...well felt beautiful anyway while wishing for high heels and longer hair. Staring at my reflection for a very long time, I would twirl and turn to see as many angles as I could.

That was my very first time and one that will never be forgotten. Those clothes and suitcase was like a dream factory for the next two months. Just before thanksgiving day everything was gone...no longer in my closet. I had been at my Aunt's house all day working the farm. After dinner I had washed up and headed for my room and the suitcase and contents were gone. Nobody ever said anything about when or why and I was afraid to ask for fear of giving everything away. I always wondered if my parents knew...There was two close calls on being caught...I doubt it as they would have been furious. To this very day, it was the best day of my life.

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8 Replies
Ambassador
(@jacquelinelarkspur)
Joined: 1 year ago

Famed Member     Gateshead, Tyne and Wear, United Kingdom
Posts: 1497

@alana1955 

Wonderful memories, Alana, and beautifully described. That first time is such a magical, enlightening experience for us all, isn't it. And I can well imagine your feelings when you discovered the suitcase gone. Something very similar happened to me when I was 14.

Thanks for sharing.

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Ambassador
(@lucyb112)
Joined: 2 years ago

Noble Member     Staffordshire, United Kingdom
Posts: 1005

@alana1955 

Great memories Alana.

I can’t quite remember my own actual first time trying anything on. I just remember a period in my early teens when left alone at home in the evenings when the urge to try on female things just came from apparently nowhere.

I can definitely remember the wonderful feeling of trying on hosiery. It’s hard to believe that was almost 50 years ago! 

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Duchess
(@pattyphose)
Joined: 9 years ago

Famed Member     Long Island, New York, United States of America
Posts: 2296

@alana1955 I can so well recall those first time feelings. Whether it was putting on stockings and hooking up the garters, wearing sheer to waist pantyhose, the experience of walking in heels and the clicking, the feeling of wearing a bra, getting dressed femme and putting on a wig for the first, then looking in the mirror and seeing a sexy girl with pretty hair looking back.

Then of course there is going out for the first time, your first interaction with another person when femme, and buying your first femme item when femme. These are such incredible feelings and experiences like nothing else.

I so understand your feelings that came out of that suitcase.

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Lady
(@alana1955)
Joined: 1 year ago

Eminent Member     Michigan, United States of America
Posts: 10

@pattyphose Thank you Patty. Every first for me was so exciting.  Just glad I don't feel like I am the only one anymore.

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Duchess
(@pattyphose)
Joined: 9 years ago

Famed Member     Long Island, New York, United States of America
Posts: 2296

@alana1955 It also seems to me that every time out is like another first. The feelings don't fade or go away.

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Lady
(@jillannquinn)
Joined: 4 years ago

Noble Member     Reno, Nevada, United States of America
Posts: 627

@alana1955 Alana, Thank you for sharing your sweet and endearing story. It sounds like a magical time in your young life. My first time was only a pair of my sister’s panties when I was 15, but I remember that experience very well. The feeling was electric and unforgettable. It was the first time I ever felt feminine and that was just a beautiful and unexpected bonus. I still feel that way when I dress and I wouldn’t want it any other way!

Hugs, Jill

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Lady
(@alana1955)
Joined: 1 year ago

Eminent Member     Michigan, United States of America
Posts: 10

@jillannquinn Thant' why I dress when I can...THAT feeling of being beautiful.

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(@brittney2016)
Joined: 6 years ago

Prominent Member     Cincinnati, Ohio, United States of America
Posts: 907

@alana1955 Thank you for sharing your first time dressing with female clothes story. An old saying; opportunity falls in your lap. In your case, it fell off of a car and into your lap.

Also in reference to your reply to JJ; I also had an Aunt B. She was my Grand Aunt; my Grandmother's sister. My Aunt B's clothes were the first female clothes I tried on. I give a bit more detail on my profile page; feel free to view it sometime.

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Posts: 2172
 J J
Lady
(@jjandme)
Famed Member     California, United States of America
Joined: 5 years ago

Oh, how I know that feeling.

I was home alone from school one day and totally out of the blue I decided to put on my mother's clothes. I had always been interested in lingerie and loved to peruse the Sears catalog lingerie section, but I never thought about wearing such things. I just started to look at and feel things and was enamored by the soft and silky fabrics. Soon I was putting things on and one by one I ended up fully dressed and even out on her wig. The sensation was amazing, and things fit reasonably well, including a pair of high heels. The stockings were the best, but attaching them to an.open bottom girdle was a challenge.  The bra went pretty smoothly, and when the dress fell into position as I put it on over my head I was in absolute heaven. I walked around the house for awhile and as I did, I became extremely aroused and I just couldn't help myself so the session ended well.

I had no concept about crossdressing at that time, and other than one other episode didn't even think about dressing for many years. One I slipped on my wife's panties years later did I realized how nice dressing en femme was and my thoughts of that first time came back. I wore just panties for a long time, then slowly expanded my dressing and now dress fully en femme and enjoy outings dressed.

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1 Reply
Lady
(@alana1955)
Joined: 1 year ago

Eminent Member     Michigan, United States of America
Posts: 10

@jjandme Looking back, I never ever changed into my mother's cloths once... nor for that matter my sisters.  I did so much want to emulate my Aunt B. She was so elegant and dressed so well.  To this day when I dress it is with her in mind.  If I could have spent more time at her house it is a very good possibility that  it would have been her clothes that found it's way onto me.  Thank you for responding and it's nice to know that I was not alone.

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Posts: 3446
Hostess
(@ab123)
Illustrious Member     Surrey, United Kingdom
Joined: 5 years ago

For me those early beginnings never ended.

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1 Reply
Lady
(@alana1955)
Joined: 1 year ago

Eminent Member     Michigan, United States of America
Posts: 10

@ab123 Me too....though a long time ago...it feels like just yesterday.

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Posts: 38
Lady
(@jo2je)
Trusted Member     Maryland, United States of America
Joined: 2 years ago

That is awesome! At first it’s like “wow, I’m not supposed to like this, but I like this!” 

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1 Reply
Lady
(@alana1955)
Joined: 1 year ago

Eminent Member     Michigan, United States of America
Posts: 10

@jo2je I agree so much with you.  Still does to this day!

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Posts: 2172
 J J
Lady
(@jjandme)
Famed Member     California, United States of America
Joined: 5 years ago

I was probably in middle school when I dressed for the first time, but there was never any thought that I shouldn't do it, it just seemed like a fun idea, and something new and different. 

As I have said before, I didn't even think about dressing for another for quite some time. In the meantime I had known several LGBT people and had an excellent class in human sexuality, so when I did put panties on again there was never an issue of it being wrong, it was just not typical.

...and there is nothing wrong with not being typical.

 

 

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Posts: 2111
Hostess
(@cdsue)
Famed Member     Delaware, United States of America
Joined: 5 years ago

Alana -

Thank you for sharing your story, and everyone else for sharing your experiences.

Like most I started when home alone after school trying on my mother's things. At first it was a curiosity, I found I liked the feel and then would put her things in when I had the chance. After a couple years that stopped as I didn't have time to be able to do it. My next experience was in college for Halloween when I went ot a party fully dressed. My girlfriend helped me dress in her clothes (bra, panties, pantyhose, dress, shoes), put make up on me and styled my hair (I had shoulder length hair at the time). I was nervous but had fun. Those are my earliest experiences.

XOXO
Suzanne

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Posts: 19
Lady
(@satinfeelsgreat)
Eminent Member
Joined: 8 years ago

as a child growing up in London, I did a morning paper round and sometimes found bags of clothes put out for charity collection on my morning round. i had in my bedroom a large wooden ammunition box for storage so picked up items and stored there. at some point my parents must have looked in and it was removed and my father slippered my backside as punishment, the only time he did that. i am now in 70s and dress every day, so it didnt work...

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1 Reply
Lady
(@alana1955)
Joined: 1 year ago

Eminent Member     Michigan, United States of America
Posts: 10

@satinfeelsgreat I think if my parents knew it would have been the same punishment for me.  Being close to 70 myself I remember those times and I always felt alone.  But not now....LOL

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