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Never Forget The First Time

10 Posts
8 Users
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Posts: 594
Lady
Topic starter
(@myfanwy)
Honorable Member     Mid Glamorgan, United Kingdom
Joined: 6 years ago

My first ever proper dressing session is imprinted on my mind forever.At the age of twelve,I finally plucked up the courage to take a pair of my mum's tights from her drawer and try them on.Cannot remember the exact shade but they would have been flesh coloured in natural.First thing I noticed was that they fitted me which did surprise me as I was very short at that age.Second thing I noticed was how nice my legs looked in the tights.I looked just like all the girls in my class in school that I so wanted to be.I did not wear a skirt ss I didn't think my mum's skirt would fit me.instead,I wore a yellow tanktop and my soccer shorts.That was okay as hotpants were in for girls back in 1972.I do not think I was dressed for long as my parents were out and I didn't want them to catch me.It was an interesting experiment which worked anf reinforced my opinion that I wanted to be a girl.I wore football shorts on sunsequent sessions but later found out that my mum's skirts fitted me which was great.When I went into my high school clsss the next day,I could not stoo thinking of my first time in tights which fortunately turned out to be the first of many.

 

 

 

 

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9 Replies
Posts: 594
Lady
Topic starter
(@myfanwy)
Honorable Member     Mid Glamorgan, United Kingdom
Joined: 6 years ago

Hi Samantha that's a great story.That was nice of grandpa not to say anything.My other crossdressing experience before my official one was when I was ten.I visited my Aunt quite often,She had three daughters,the youngest was the nearest in age to me,she was five years older than me.When she got to about 12 or 13,she started to wear hose,I was so envious of her.One night,I begged her to let me dress in her clothes and her pantyhose.Don't think she was too happy to let me wear her hose which is understandable.She did allow me to wear one of her dresses,which was green and quite long.My cousin and her girlfriend put makeup on me.I loved it took to it like a duck to water and loved the feeling of being one of the girls.Fun was over too soon though,my father came to take me home,Off went the clothes and the eye shadow.My dad who was very much a man's man and would not encourage that sort of thing at home was very good about it and probably thought that my cousin dressed me up for a joke.A year or so later my cousin and two of her gal pals had they photos taken on a bench on some parkland in our village.The bench was for charity and the girls helped raise money for it.When I saw the photo I was so envious as they were all dressed in pretty clothes and all wearing hose.I so wanted to be the fourth girl in that picture.Even now,I wish I could be a twelve year old girl and be superimposed on the picture.

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Posts: 1
Lady
(@gerryc45)
New Member     Ayrshire, United Kingdom
Joined: 6 years ago

when i was 14 i think when i tried on my sisters clothes ..at first i didn't know how to pull tights up but i soon learned ..i had to roll them up of course !..oddly enough when i was dressed as a girl i felt this very comforting relaxing feeling,it was almost overpowering like a drug but much more pleasant ..iv'e never done drugs so i'm just surmising ..we had this large park near where i lived and i used to walk my dog there dressed as a female,i would see people in the distance and they would look at me but not staring if you know what i mean,i was just another girl ..i had this black bob wig,i wore a pleated black skirt with brown tights and also on other occasions blue tights ..i always wore white or pink underwear ..i did this for i think 4 years every day ..the wet days i had an umbrella ..one time i recall this girl had her dog and we were quite a good way away but she complimented me on my dog and stuff this was really quite thrilling as she regarded me as another female..such joy and happiness !.i take my name Fiona from the lady in the library who always dresses in very feminine clothes and she's so pretty and the lady i would like to be..but,i can dream..such sweet and lovely dreams ..the delights of being female..tender soft dreams of being the girl i know who resides in my soul..forever .

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Posts: 4563
Managing Ambassador
(@willajay)
Majestic Member     The Middle of Nowhere (TMoN), California, United States of America
Joined: 6 years ago

I was playing hooky because I didn't have an assignment done; mom let me stay home alone when she went to work. probably 3rd or 4th grade.

I went all through her stuff that day.

the only thing she said to me that night about it was she asked me privately if I'd had fun with her makeup.

it became a couple of times a year thing for me after that.

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Posts: 104
(@stephaniegirl226)
Estimable Member     Wisconsin, United States of America
Joined: 8 years ago

My first time was when I was 14. I very short slim and had long hair. A few days before I boarded a bus and driver called me a young lady. After that I wondered what I would look like as a girl. I was going to be home alone all day. I tried on my older sister and mothers clothes. I tried on everything imaginable. My sister had a wig. My mother had this beautiful pink slip. I had so much fun I was hooked. Whenever I had extended time alone I would dress up.

 

One day my sister came home unexpectedly. I was fully dressed in wig, high heels, skirt, bra, pantyhose and sweater. Luckily I had chain lock on the door. I ran into my room quickly disrobed put on a pair of my shorts and answered the door. I gave her an excuse I was going to take a shower. Glad I did not get caught.

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Posts: 0
Guest
(@Anonymous)
New Member
Joined: 1 second ago

I started young. I remembering wearing one of my mom's all-in-ones and one of her dresses. I was so thrilled! Never gave any thought to my brothers coming home from school early. Didn't get caught though..

 

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Posts: 594
Lady
Topic starter
(@myfanwy)
Honorable Member     Mid Glamorgan, United Kingdom
Joined: 6 years ago

I started young. I remembering wearing one of my mom’s all-in-ones and one of her dresses. I was so thrilled! Never gave any thought to my brothers coming home from school early. Didn’t get caught though..

No,neither did I thank goodness.

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Posts: 907
(@brittney2016)
Prominent Member     Cincinnati, Ohio, United States of America
Joined: 6 years ago

When I was 9 my grand aunt allowed me to go through her 2 main clothes closets and pick out all her dresses that I liked plus her panties and slips. We put everything in a large box that we slid under her bed so that everything would be available to play dress-up whenever I would spend the night. My favorite dress of hers, was a royal blue soft material dress with white polka-dots and long sleeves. I always matched it with a black panty and a black full slip. Since she was a rather tall lady and me be being about as high as her waist, the dress fit me like a prairie dress. It was that way with almost all her clothes, but I loved that dress. When we got tired way later at night, she would let me sleep in the dress as a nightgown over my pj's. I was always worried about wearing the panty and slip instead of my pj's, in case my mom came early to pick me up the next morning. I wish I had slept in the panty and slip, as I always woke up before she got there.

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Posts: 121
Lady
(@susanzed)
Estimable Member     North Yorkshire, United Kingdom
Joined: 6 years ago

I was five or so when I found a bag of my mums panties under her bed and going through them found a flowery soft nylon pair. I took off my pj's and slipped them on. It felt great and I remember bouncing on her bed in them having fun but then thought that I should sleep on them I didn't because it occurred to me that she might get cross that I was touching her things. A few years later my sister and I were playing at home when our parents were out and she suggested I wore one of her party dresses. It was purple and wS made of some shiny material and was pretty and felt lovely to wear. She also gave me  pair of purple cotton knickers and white knee length socks to wear. Running around the house in that outfit was fab and the feeling of freedom and the cool air floating up the dress to my sisters knickers felt so wonderful. From that moment I was hooked. 

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Posts: 2296
Duchess
(@pattyphose)
Famed Member     Long Island, New York, United States of America
Joined: 9 years ago

I was fascinated by women's legs in nylons for as long as I can remember. So much so that at 4 my mother gave me stocking to play with so I would leave the ladies alone. The stockings never stayed up so I started getting pantyhose. One day I noticed a pair of my mother's pumps and put them on. With my shirt that looked like a short dress, my pantyhose and the heels, I would happily and proudly go prancing and clicking about showing off my pretty lady legs.

Moving forward over the years I had a lot more memorable firsts but these are my early beginning ones.

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