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  • #423811
    Rosydoo
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    Registered On: July 15, 2016
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    What started it all, I thinkI have thought about this a lot. Read many books on crossdressing and related topics. Have seen a therapist quite a few times with my wife. Always wanted to put a label on what I am. Label not so important anymore, I’m just me. But what I really wanted to share is that I always suspected that my crossdressing desire started in 3rd grade when I was in a play and today I found an old photo of my parents from the play and I’m pretty certain that that is what started this adventure. The play was not so much a play as all the students in the class were dressed up/staged to emulate a famous historic paintings. I think it was called “Living Pictures”. In any case, I was 8-years-old and dressed up as “young Henry VIII”. Although I was dressed as a male of the 16th century, in my eyes I was all girl and something clicked in me. I had a curly blonde wig, a skirt, hose, red lipstick, mascara and other makeup. I vaguely remember the strange feelings as the mothers put lipstick, mascara, etc. on me. I think this definitely was the beginning of my crossdressing adventure.

    • This topic was modified 3 weeks ago by Stephanie Flowers. Reason: Move to another forum
    • This topic was modified 2 weeks ago by Rosydoo.
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    • #432460
      Jessie G
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      Registered On: December 31, 2020
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      Does anyone remember Flip Wilson who crosdressed on his variety show? That kind of sent me in this direction. I was caught in my teens by my mother in her panty hose. She really didn’t say much but she did mention it a year or so ago but as one of the boys not me particularly. But dress up in mums things was always fun.

      kisses Jessie

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      • #433230
        Krissy Richards
        Registered On: June 11, 2020
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        When I was little it was everywhere and even my hero David Bowie was doing it so if its good enough for him its going enough for me

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    • #432459
      Rami Love
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      Registered On: November 30, 2018
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      It started with me playing with my mothers things from before I can remember, earnings, makeup, perfume, her clothes. I actually did not start cross dressing for real until my mid twenties. I really did not have any desire to cross dress in my teens and early twenties. I was more interested in chasing girls than becoming one.

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    • #432450
      MelanieElizabeth
      Lady
      Registered On: January 9, 2021
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      For me it started around 6 or seven years old. We had a family member staying with us over the summer and she had a one piece bathing suit that intrigued me. I don’t know why but I wanted it. After everyone fell asleep I put it on under my blankets. At that age I didn’t know why I enjoyed the feeling and I still don’t to this day. The urge seemed to go away for a few years until one morning i noticed my mother getting ready for work and she was wearing a pair of pantyhose and flats. Something triggered in my head at the age of about 10 that I had to put those things on. I couldn’t wait for my siblings to go out so I could have the house to myself. After putting on her pantyhose and shoes I was in heaven. Really from then until now I am drawn to dress. It started with other people things as a youth until now I have a hidden stash which my significant other has found. I can’t avoid it for too long the pull is strong and whenever the opportunity arises I can’t resist. I have never gone out in public and don’t feel the need to but dressing is a part of me. Don’t know why but I just enjoy it. Lately I’ve taken it further makeup, false lashes, breast forms etc. I love looking in the mirror and seeing the transformation.

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    • #431851
      Wendy Swift
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      Registered On: May 11, 2020
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      Oh my, there are so many events in my life that started my path to CDing, and all played a factor on how I started :

      – my mom would always wash her pantys and  let them hang on the bathroom rack to dry.  As a small kid, everytime I had to use the washroom, I would look at the pair of pantys with just wondered how they felt.  One day I did just that, I touched them and noticed immediately how soft and smooth they felt.  I was a latch key kid, so I had alot of alone time until my parents came home from work.  One day curiousity got the best of me so I tried them on.  My goodness, they were heavenly !  The panties felt so smooth and soft against my skin, I was extremely delighted.  Naturally since I was a small kid the panties were big on me, but yet it felt “snug” enough at the same time.

      – christmas play in elementary school.  I played an elf and the teacher said we had to wear leotards (or tights).  I didn’t have any, so a girl piped up and said she would loan us some tights.  I wore them, but at a young age I didn’t notice anything about them and because they were girl clothes, I could not wait to change back (ironic now !).

      – in kindergarten, the whole class went to the pool to swim.  There were adults who would have us strap onto their backs and they would swim from one end of the pool and back.  I didn’t have any swim suits, so at that time the pool had loaners.  Well, they ran out of boy swim suits and had only girl one piece suits so they gave me one.  I can’t recall how it made me feel, but I splashed and played in the shallow end wearing that one piece suit being as happy as can be.  I think that event led me to my fascination with women’s one piece swimsuits, especially the racing kind.

      – my early teen years was when I started to notice girls and how they dressed, their hair, makeup, mannerisms, …  I remember watching my all time fave tv show Three’s Company.  I noticed how well Janet would dress, in a tight pencil skirt, sometimes with a thin gold belt, and a nice blouse (well, for the 80s anyways).  I also noticed Janet’s heels, I wasn’t pumps but I was attracted to her shoes.  I was immediately drawn to that type of outfit.  I began digging into my mom’s closet and found articles of clothing that was similiar to what Janet wore, but not exact.  She did have straight skirts, and some blouses so I made the best of that.  I loved that type of outfit, and to this day Wendy’s wardrobe consists primarily of pencil skirts, blouses, and blazers, similiar to what Janet wore on the TV show (minus the blazers).

       

      There are other events that led me down the CDing path, for instance working downtown I would admire women who would wear the office skirt suit, looking so sexy and professional.  Watching the summer olympics, especially the women’s swimming and high diving as they would wear the snug one piece suits that I most admire.

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    • #431479
      Requal Joanne Jones
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      Registered On: December 15, 2020
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      My sisters dressed me as a girl when I was young. That is how I commenced my journey in the cross dresser’s world.

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    • #431463
      Kitty Van Curen
      Lady
      Registered On: November 3, 2020
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      I first felt alight at such a young age I’m unsure how old I was! I was very young though and it was at Christmas, my sister got an amazing gold pair of high heels, I was allowed to try them on and was mesmerized by them, I just adored looking at my feet in them which resulted in tantrums when they were taken away from me. The whole sensation ebbed for many years until I was a teen, I would on occasion wear something like a dress, but it never transpired to much. I was too distracted with schooling and career focus. I came into my own when I left home, that’s when things really opened up for me. I expanded a wardrobe, rapidly, accrued shoes, bags, accessories. I became overwhelmed with desire for all of it. Now it’s my identity, who I am. Completely.

      Thanks!!!

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    • #431449
      Cheryl Moss
      Lady
      Registered On: January 12, 2021
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      Hard to pin point for me… when I was 10/11 I used to write stories in which I was a gay male who would spend weekends away from his wife with a male lover (strange I know and especially at such a young age). In the stories I would dress as a woman. At this young age I didn’t really know what this meant and why I wrote about this but i used to look in the catalogue at the lingerie section which helped in my story writing. The first item of clothing that intrigued me was my sisters navy blue gym knickers. I tried them on and that was it… I moved on to other items of underwear and it snowballed from then on.

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    • #427956
      Ashley Konners
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      Registered On: August 15, 2020
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      What started me what I can remember was seeing my moms and sisters pantyhose hanging over the shower curtain drying, looking at the lingerie in the catalogues and often wondering what it would feel like to wear such things.
      I remember being home alone and be drawn to my sisters room and looking in her closet at her dresses and skirts. I was to scared to try them on so I went to her dresser and started opening drawers. The first one was her panties and I touched her white silky ones, Next was bras and some slips and camisoles. Then I hit the jackpot… the pantyhose drawer. These already had my attention and I knew I had to try them  not knowing why I was feeling this way.I took out a pair of beige all sheer.(knowing this now but not then) I very awkwardly started to pull them on. Then I remember watching my sister roll them up and starting at her toes. I sat on the edge of her bed and tried this technique which worked much better. The feeling that came over me was amazing, they felt nice on my young hairless legs. I was hooked right then.  Even though they felt great my nerves took over and only having them all the way up and on for maybe a few minutes I removed them and my heart really starting pounding when they didn’t look like they did when I took them out. I figured she would notice so I put them on the bottom of the pile. After a few more times doing this I keep a pair and put them in my room. I put them on every chance. I also remember putting her lipstick on and clear nail polish. Then in time I needed more so I try on one of her slips.  Omg the silky slip on top of the pantyhose put me over the edge.  The emotions running through my 12 year old head was crazy.  Why do I like girls things , I’m a boy.  I must be the only boy doing this.
      Anyway to make a long answer short that’s what started my crossdressing for me.

      Thanks

      Ashley.

    • #427878
      DeLora
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      Registered On: October 15, 2019
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      I think my crossdressing is an expression of my gender identity and I suspect that is something essentially genetic with minor environmental influences that has always been a part of me.

      My desire to dress, or explore femininity, goes back to when I was probably about 4 and first started to notice things like how girls had their hair in pigtails or braids, how they had pretty little air clips or hair bands. I wasn’t ’till I was about 8 that I had the first opportunity to do any crossdressing. We were given a bag of assorted clothes, mostly socks from a relative. In that bag of socks I found a pair of blue, wool tights. I hid them away and eventyally plucked up the courage to try them on.
      I wouldnt say it was these tights that got me started, they were just my first opportunity.

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    • #427816
      Genevïéve
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      Registered On: July 28, 2020
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      In mother’s heels at 3 y/o (photograph), my earliest ‘recolection’ of wearing a feminine article of clothing was at at approx 5 y/o… I tried on a pair of mother’s silky granny panties. She caught me and as a result, was severely scolded.

      Don’t recall much more until about 10ish. when I developed Gynecomastia and had a thing for bras. At one point almost filling a D cup.

      My dressing was on and off until a few years ago when it escalated. Bought some clothing, forms, make up, jewlery, nails etc. online. Dress in my ‘Comfies’ almost every day. It is very difficult to do without.

      As to ‘what’ drew me to those panties at 5 y/o… don’t recall. Probably the feel of the material and just had to try them on.

      Gen… 💋

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    • #427809
      Stephanie York
      Lady
      Registered On: May 22, 2017
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      I remember seeing crossdressers on TV when I was about 14. I also had longer hair and was often mistaken for a girl. I was going to be home alone all day and was curious to see how I would look dressed up. My older sister had a wig and was about the same size. I tried on so many different outfits. I liked the way I looked and the rest is history.

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    • #427780
      Heather Jameson
      Duchess
      Registered On: April 1, 2019
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      About the only thing I can come up with is curiosity and admiration. I have a beautiful sister 9 years older than me and she was very fashionable, I always admired her. O ne da when I was 10 I was home alone and spotted some of her stuff on her bed, curiosity kicked in and I tried on her panties and nylons. That was it, next it was the bra, then a dress and of course you’ve got to have heels. That was it, I was hooked, but as for an actual reason why, I haven’t got a clue. I’ve read quite a bit about this and the best I can figure is this is how I’m hardwired and that day just closed the circuit and here I am.

       

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    • #427721
      Sarah Lacy
      Lady
      Registered On: April 4, 2020
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      Hi Rosydoo,

      I often look back and ponder the question where did it all begin and sometimes why?

      I first started dressing I think at the tender age of 5 or 6. My sister (2 years older) and I used to play dress up whilst visiting my Granny once a week. My sister was dressed in girly clothes and for some unknown reason I used to put on Grannys stockings and shuffle around in her oversize shoes. Neither fitted me, the stockings were about 5 sizes too big as were the shoes but I can still remember that tingle as the nylons slid over and about my legs, in those days my legs were always bare as young boys wore nothing but shorts. It could not have been sexual as I was far too young for that but it was sensual, if that makes any sense.I know that I longed for those visits so we could play and remember the arousal to this day.

      This I think sowed the seed of my liking for nylons and the need to feel them against my skin. Even whilst writing this I can still remember those feelings and the smell of new or freshly laundered nylons as we played so innocently. The same feelings are aroused even today when I pull stockings up my legs and I briefly hark back to the memories.

      In later years with my sexual awakening I found and wore stockings that had either been discarded or put in the laundry basket for washing. I also lusted after the gorgeous models on the packets that the stockings came in. When alone in the house it just seemed so natural, yet again so wrong to seek out sexy clothes in my mothers’ or sisters’ bottom drawer to wear and enjoy.

      Humble inocent beginings but a lifetime of guilty pleasure.

      Sarah.

    • #427686
      Serena Stevens
      Duchess
      Registered On: December 30, 2020
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      I’m not sure what provoked me to explore my mother’s panty and nylon drawer as a teenager; however, my love of cross dressers skyrocketed with shows like Ricki Lake, Sally Jesse Raphael & Jerry Springer. There was something about this “escape” that was a turn on. Watched a Ricki Lake episode last night on YouTube and remembered how stimulating it was and is to see girls who used to be guys. Makes me dream of transitioning.

      Too many years later -but not too late – I have finally stopped running from the woman in me. Long, live Serena, and long live our CDH “sorority.”

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      • #428542
        Krissy Richards
        Registered On: June 11, 2020
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        I think it started for me after my nan died as was sorting her stuff out like her clothes and i had this urge to try on some tights then the next day a corselette and a dress and before i know it was doing it everyday! This went on til i moved out then i would go out on a friday night and wake up the next morning dressed in a stockings and a corset id bought when i was drunk? Then i started shaving all my body hair offand dressing up in my room and going out late at night dressed as a woman and also meeting girls like us and having fun playing with each other experimenting with make up being more and more of a woman but holding down a man job. Then out of the blue got married but carried on making sure i never got caught by wifey then recently we broke up and here i am doing more of what i fancy which is dressing like a cock teaser and being hot, as im sure my middle age slut version of krissy is kicking in as i wear the highest heels and the shortest skirts i can buy and the most sexy lingerie i can find and it has to be in black or red. So ive turned into a middle aged hooker looking woman, which i love as i like having a edge to me and being like nobody else. Ive come to the point where ive no shame and go into womens shops and ask if they have that dress in my size i feel so liberated and love 💘

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        • #428560
          Krissy Richards
          Registered On: June 11, 2020
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          I can remember bumbling about in lingerie sections when i was younger i used to be so scared but i just dont care, ive even tried a dress on in marks and spencers when dressed as a bloke one day after work! The old woman was asking me ifit was right size and if the bra was the right cup size bless her dont care im me and i dress like this sometimes? Most times this is my life and i love the feel of it

        • #428547
          Krissy Richards
          Registered On: June 11, 2020
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          Think id shave the body hair off regardless of whether i dress or not as never liked having body hair as i feel dirty when i have had anyso it gets shaved or waxed off regularly

          • #428549
            Krissy Richards
            Registered On: June 11, 2020
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            I think the woman has always been in me as i used to look at womens tights in catalogues and gaze at the lingerie section too and dont get me started about tights sections in shops could happily look thru every pair of tights in a department shop all day

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          • #428587
            Krissy Richards
            Registered On: June 11, 2020
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            Its like when i go in asda or tescos im looking out the corner of my eye at the tights and lingerie section or looking at what dresses or skirts they have? As a girl needs nice things and you can never have enough dresses or skirts. Ive got to go food shopping later and i expect ill end up buying something to wear later on today as already got my eye a wonderful denim skirt in a supermarket thats really cheap And fits me lovely as ive a black one and i want the blue one now.us girls love a bargain and i will look real cute in it too. X

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          • #428566
            Krissy Richards
            Registered On: June 11, 2020
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            Its got to the point now where i dont care and ill buy anything and try anything on in a womens shop to think its allowed 🙂

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      • #427803
        Krissy Richards
        Registered On: June 11, 2020
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        Yes I know what you mean I don’t know where it came from but once you start you have to continue and become the woman you dream of being. I dress fully but I don’t wear make up maybe thats what I should do next. As I need to see this thru as I dress fully and wear heels

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        • #428553
          Krissy Richards
          Registered On: June 11, 2020
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          This time im taking it all the way as ive just bought heaps of clothes for myself and im so excited 😁 for when they come and bought a pair of the highest heels ever! You only live once why not

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      • #427739
        Krissy Richards
        Registered On: June 11, 2020
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        I think my femme genes have always been there and that’s cool. I’ve gradually come to terms with it. I

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    • #427680
      Belle (Ellie) Porter
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      Registered On: January 4, 2021
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      When I was about 4, I had a dream where I was dressed up like Belle from Beauty and the Beast. I’m struggling to remember exactly how I felt. I remember the next I just felt very strange, and I didn’t tell anyone. Since then I fantasized about wearing a gown, having long hair and makeup.

      I didn’t actually dress up in woman’s clothing until I was around 12, where I wore panties. I remember It felt really good!

      I still haven’t dressed up completely like a woman yet. I have a little makeup, a wig, and a dress, but that’s it. I don’t have much money right now and I’m trying to save up, so I’m hesitant to get much else.

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    • #427656
      Jasmine Secrét
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      Registered On: August 5, 2020
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      My first time wearing anything feminine was panties. First, just for the wife, once in a blue moon before we would have some intimate play. It was not long after, maybe a year when I was “playing” with a gentleman and he asked if I would wear nylons while we played. They felt so wonderful….it just went upwards after that. Panties, and nylons. Then, lingerie, and wigs; heels soon followed as did makeup and jewelry. Jasmine was born later. She is shy and isn’t out.

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      • #427933
        Anonymous
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        Jasmine might not be out publicly, but your sisters here know and love you!

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    • #426122
      Dee
      Registered On: December 31, 2020
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      What started it all, I thinkI have thought about this a lot. Read many books on crossdressing and related topics. Have seen a therapist quite a few times with my wife. Always wanted to put a label on what I am. Label not so important anymore, I’m just me. But what I really wanted to share is that I always suspected that my crossdressing desire started in 3rd grade when I was in a play and today I found an old photo of my parents from the play and I’m pretty certain that that is what started this adventure. The play was not so much a play as all the students in the class were dressed up/staged to emulate a famous historic paintings. I think it was called “Living Pictures”. In any case, I was 8-years-old and dressed up as “young Henry VIII”. Although I was dressed as a male of the 16th century, in my eyes I was all girl and something clicked in me. I had a curly blonde wig, a skirt, hose, red lipstick, mascara and other makeup. I vaguely remember the strange feelings as the mothers put lipstick, mascara, etc. on me. I think this definitely was the beginning of my crossdressing adventure.

      • This topic was modified 3 weeks ago by Stephanie Flowers. Reason: Move to another forum
      • This topic was modified 2 weeks ago by Rosydoo.

      I was 13 my sister 17 she was getting laid had sexy panties and some tight out fits she also rode the stair banister I could not help but to do what she did the way she was dressed when the opportunity presented it self I would wear her clothes and ride that banister and anything else it made me feel great and I am now stuck with feeling great every time I get dressed

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    • #425503
      Angela Booth
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      Registered On: August 1, 2020
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      My mother reminded me of a fancy dress competition when I was years four years old. She dressed me as a ‘Lady’. long dress, fur stole, make up and a tiara. I won the competition but I was so young I have only vague memories. After that I began to realize that girls clothes were far more colorful than my boys clothes. While playing with my sisters I would occasionally dress up and it was seen as fun and there were no adverse comments. I felt very normal when dressed.

      Things began to take hold when I started to secretly dress and wear their underwear. This went on for many years and I would still dress for fun culminating in a beauty competition where I was fully dressed and won a nice cash prize! I was about 13 at this time and still dressed in secret. I knew I liked the image and was always seen as a girl when I dressed. I always had a more feminine side than male.

      Once I reached puberty dressing fell to the wayside but was till in my mind and taken up when the opportunity presented itself, usually for fancy dress parties.

      By middle age I returned to my dressing and began the journey to where I am today. Once I started to come out to family and friends, and discussed my evolution, people would always think that as I was allowed to dress in the family circle it was my mother that was the catalyst. I don’t think so. She was the first person I came out to and assured me she didn’t have a clue that I dressed in secret and had desires to be the person I am today.

      Inadvertently I think that she allowed the real person space to grow.

       

    • #425308
      Jennifer Lynn
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      Registered On: August 15, 2020
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      I remember exactly how it started. For some reason I didn’t know then my wife bought bought me a couple pair of panties to wear around the house. Not long after I she had replaced all my male underwear with panties and informed me that was the only underwear I was allowed to wear. Soon after she gave me a couple bras and was told to wear. What followed was my male clothing was slowly being replaced with skirts, dresses, women’s Jean’s and slacks, blouses and tops. That continued until my entire wardrobe was all female. During that same time frame she bought my first wigs, shoes, lingerie and she taught me how to apply makeup. She created Jennifer.

      • #425426
        Jessie Monroe
        Lady
        Registered On: December 27, 2020
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        Such a lucky girl Jennifer to have a spouse like that.

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        • #425435
          Jennifer Lynn
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          Registered On: August 15, 2020
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          Thank you, and I know how lucky I am.

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          • #427743
            Krissy Richards
            Registered On: June 11, 2020
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            wow your so lucky, im pleased for you. I’ve always known i was different? I’ve always shaved my body and dreamt of being a woman 

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          • #427767
            Jennifer Lynn
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            Registered On: August 15, 2020
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            Thank you. When she 1st started my transition I had no idea where she was going with it. If I had back then I most likely would have stopped it. But as it turned out I am so glad I didn’t know. I have never been more happy in my life than since Jennifer was born.

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    • #425295
      ChloeC
      Duchess
      Registered On: November 5, 2019
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      I’ve mentioned several times that I vividly remember a summer day when I might have been 4 or no older than the next summer when I was 5 that I asked my mother to make me a dress. And she did, a full dress out of kraft paper and I played in it that afternoon in the yard until it tore.

      Thinking back on all that I have come to realize that to make that request I must have thought rather deeply about it, and me, for a significant amount of time before that moment. I’ve never been as far as I can remember an impulsive person. I like to think about things a lot before I tend to act upon them.

      And now some complexity enters in. My father died in an accident in the fall of my 4th year and my mother was devastated.  I had an older and a younger brother and I suspect she had hoped for a girl with her 2nd pregnancy . I also am more emotionally open than my siblings and she might have turned to me for some solace and being me I might have wanted to do what I could to meet her desires…or not.

      I suspect a therapist could have a field day with me but over the years my feelings and desires have grown and become much more specific even with her sort of finding out and admonishing me. So maybe not.

      Alli do know is I started then and quickly learned to keep it to myself and explore it more and more as  the feelings only increased and I grew up.

    • #425288
      Clara Cross
      Lady
      Registered On: December 7, 2020
      Topics: 3
      Replies: 49
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      I wish I knew what started it all. Let me spend a little time on your couch if I may.

      I have a vague recollection of playing, “show me yours, I’ll show you mine” with a neighbor girl. I remember getting caught by my mother. It wasn’t really crossdressing at all but an intense episode of curiosity about what girls looked like under their clothes. I was only four or five at the time. Its really remarkable that a rather innocent incident like that can stick with you for half a century. Holy cow! (Anybody have Freud’s phone number?)

      I also have memories of sneaking my sister’s undies out of the laundry hamper occasionally. It wasn’t frequent and didn’t become the compulsion it feels like today. It did feel a little bit naughty, but it certainly felt nice too. That was maybe age 12 or so.

      In my teen years, and this will really date me, fashions actually took a turn towards the femme for awhile. Remember those disco years when men’s heels were in style? And synthetics became the go-to fabrics for men’s shirts and pants? And it was probably around then that “panties” for men became available as well. I am guilty of all of the above. Thank you John Travolta.

      Then most recently, at age 50 something, I was gifted with a couple pair of those men’s style panties.You know. All silky with the extra pouch in front. Although I didn’t love them, I wore them. They felt much better than they looked. The point is, at about this time a desire, a need maybe, developed and I found myself getting up the nerve to buy pantyhose and then real panties. It was an almost unconscious decision. Just felt like I had to do it. Turns out the shopping was as much of a rush as trying those lovely things on.

      Fast forward a year or two and I am having trouble finding room in the closet for the skirts, dresses, blouses, shoes and lingerie. There certainly isn’t any room in the closet for me. So I am lucky to have an understanding spouse. Now I just play “show me yours, I’ll show you mine” with her. : )
      Thanks for letting me ramble a bit,
      Clara

    • #425167
      Megan
      Lady
      Registered On: December 28, 2020
      Topics: 1
      Replies: 6
      Has thanked: 43 times
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      So, for me it started when I was around 12, maybe even 11. It was the summer before my 6th grade year I think. Me and two buddies were playing in the woods and one of them told us that he liked to wear his sisters panties. He said that it felt good, and something about how if he pulled them down just a little so you could see some pubic hair at the top thought it looked like a girl. Girls weren’t really shaving down there as much back then I guess, lol.

      Anyway, it was an out of the blue disclosure and pretty surprising. None of us had ever talked about anything like that before and he was actually one of the tough kids at school so it was doubly surprising. He did threaten to beat us up if we ever said anything to anyone 🙂 We never talked about it again, but I always wondered what happened to him or if he ended dressing fully too. Also wondered if our other friend ever tried it.

      I of course did try it. I was curious after he said that, and not long after I borrowed a pair of my sisters nylon panties from the wash and ducked into the downstairs bathroom to try them. I had honestly never looked at her stuff before and never thought twice about. I still remember they were a seafoam green bikini with some lace accent. They looked so unlike my tighty whities and the material felt so good. I slid them on and it was euphoric. They felt amazing.

      So, my sister was 4 years older than me, so her stuff fit me pretty well at that point. I remember thinking that of panties felt so amazing, what was it like to wear other girls clothes? It didn’t take me long to find out. My dad worked evening shift, and my mom was a nurse who worked shifts. My brother was in college at this point I think and my sister was pretty busy and would end up going to college 2 years later. I had a lot of time to myself as a kid to dress, and I did.

      I pretty quickly moved to adding bras to the panties, which were also amazing, I remember we had a stack of clothes that were going to be donated in the laundry room and there were two of my sisters sun dresses in that pile. Those were the first actual girls clothes I wore and I wore them a lot before they did finally get donated. After they were gone, I started looking in her closet for stuff to wear. I remember being scared and excited going through her stuff. The laundry room and donate pile somehow seemed okay, her room was a magical world of girls stuff. I know in hindsight that its a violation of a persons privacy to go through and wear their stuff, but as a kid its what I had access too, and honestly probably some of the forbidden aspect of it made it more exciting. In her room I discovered pantyhose and slips, which were also adorable. She had nice clothes too. I learned to be excited at Homecoming and Prom time because I knew she’d get some amazing dresses that I’d get to try later. She had great taste in clothes. I like to think that rubbed off on me 🙂

      At some point I started wearing my mom’s stuff too. She didn’t have much in the way of dresses, although I did try what she had, she was more a dress slacks kind of lady. At this point I wasn’t interested in girls/women’s casual looks, it was all dresses and skirts for me. She did have some nice bras, panties and slips though. Not slutty stuff, but kind of classy and feminine. She was a nurse too and actually had two nursing dresses from back when nurses actually wore white uniforms. Even as a teen it was super fun to dress up as a nurse with white pantyhose on 🙂 Again, not cool to wear your mom’s stuff although I later found out that was common. At the time though I had access to both a teen girl’s wardrobe and an adult woman’s so it was an exciting time and it definitely formed my views on style and clothing. I think that may be why I prefer real women’s fashions, rather than fetish stuff that a lot of CD’s like.

    • #424403
      Rei Durden
      Baroness - Annual
      Registered On: October 11, 2020
      Topics: 19
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      I was about 5 years old and visiting family friends at their house.
      Me and one of girls that lived there swapped clothes.
      I still recall vividly how my body looked clad in those green little tights, it was an arousing experience.

    • #424391
      Brandie Nochole
      Lady
      Registered On: October 6, 2020
      Topics: 22
      Replies: 28
      Has thanked: 253 times
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      I grew up in a family that was 95% women there was other kids on my block they was all girls. I was curious what was it like to be a girl so one day I was out sic from school I snuk into my moms closet and tried on her clothes. Thats when the switched flipped and i have been doing it ever since.

    • #424115
      Teralynn Loving
      Lady
      Registered On: October 17, 2019
      Topics: 2
      Replies: 1061
      Has thanked: 7842 times
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      Vividly! I have always been a spiritual person. Did a lot of meditation over the years. I was visited by some beings during a meditation in 2001 who told me that I had lived more lives as a woman than as a ma. That on the other side I was known as Teralynn not John. When I asked what I looked like as a woman, they replied not too much different than you do now except longer hair and bigger breasts because I always selected the same body type. Of course I was highly skeptical of this information but also intrigued. What would retired Marine John, a no nonsense combat veteran look and act like as a woman? Curiosity killed the cat they say, and it got the best of me. I just had to know what a female John would look like. So I researched everything I could about crossdressing, bought all the necessary items of feminine attire (thanks Amazon) and then on the first day I had time to myself I attempted to dress as Teralynn. After I got completely dressed including heels and wig. I walked over to a mirror and took a critical look. I was stunned beyond my wildest expectations. Could these beings actually be telling the truth? From my look in the mirror I had to admit their claims were looking much more believable. Now two decades later, Teralynn and John both have a place in this physical life and I am a happier and more complete person as a result of it. – Blessings from Teralynn

    • #423982
      Amy Myers
      Baroness
      Registered On: February 11, 2019
      Topics: 15
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      I was young, around 12 as near as I can remember and one day I looked in the laundry hamper and saw my Mom’s bra and corset on top. I was home alone for a little while and for some reason I picked the up and started putting them on. For then on I’d do that when I had the chance, till the living situation changed and I no longer had the privacy to dress. Then I didn’t get the urge again till some years later.

      Your story also brings to mind one of my own, not about me, but about someone I went to school with. This was likely about grade 6, and I can’t remember if it was a play or a Halloween dress up day, I think it was the latter. That doesn’t really matter though. I cannot remember what I wore, but I was struck by how pretty one particular girl looked, I think it was something like a circus or a ballerina outfit she wore. She was beautiful, and I could not figure out who she was, as I had never seen her before. Turned out, “she” was another boy from my class!

      I forgot about that incident for many years, but knowing what I know now I have to wonder what became of him. This is a drive and compulsion which often tends to wax and wane, but slowly gets stronger as we age. The timeline for this must have been early 60’s, which through that period was not a very forgiving nor understanding time to be trans.

      • #424003
        Jessie Monroe
        Lady
        Registered On: December 27, 2020
        Topics: 0
        Replies: 23
        Has thanked: 7 times
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        Interesting story Amy. Wonder if your school friend still dresses?

        3 users thanked author for this post.
        • #424402
          Amy Myers
          Baroness
          Registered On: February 11, 2019
          Topics: 15
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          I have wondered the same thing, and if I was a betting girl, I’d bet that he was. Must have lost track of him around grade 8 or so and now I cannot even remember his name.

          Amy

          2 users thanked author for this post.
    • #423980
      Sophia Keeler
      Duchess
      Registered On: June 21, 2020
      Topics: 3
      Replies: 39
      Has thanked: 1088 times
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      Hi Stephanie , I was 9 when I had found a box of my mom’s clothes that was stored in my closet, since my bedroom was above the garage and had a huge closet. Anyway I found some stirrup pants and a blouses and tried them on. I was hooked. Even before that I fantasized about what it would be like to be a girl. I always admired them for the clothing and the nice long hair and even that they could have babies. I know I’m a transgender, but unless my girlfriend breaks up with me ( god forbid) I will not follow through with transitioning. Plus my folks would not approve. They know about my crossdressing, but thats all they know. Have a happy new year.
      Sincerely Sophia

      • #427730
        Krissy Richards
        Registered On: June 11, 2020
        Topics: 2
        Replies: 146
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        I can remember when I was around 6years old I used to sleep in my bedroom and my mother clothes were still around as she had just walked out on my father, so I used to to sit there looking at them for ages then one day I just tried pulling on a corset of hers, ive always had this dream where im a woman and was born a girl. So after a few weeks of sleeping in acorset it just progressed and as I was alone I could pretty much dress how I liked, I loved the feel of soft stockings and how it would make me all giddy and how beautiful and sexy id feel and look. I carried on into my adult life trying to get anything feminine to wear but keeping it a secret always. Then I met a woman and had kids and I stopped for ages but it was always there, my wife would go out and id dress with clothes id bought and feel so beautiful. After a while my wife would ask questions like why do you shave your body and legs 🦵🤔 she never knew but we soon divorced then I plunged head 1st into being a woman and I so enjoyed it but I met another woman and stopped for while that relationship came to nothing and ive still carried on dressing, looking at online shopping and sometimes buying lingerie for myself. I still shave my body and legs and make time to dress and be the best woman I can be. Dressing is starting to take over my life, I dont know whether I want to dress or be a woman? Thats my story thanks for reading

        2 users thanked author for this post.
    • #423957
      Bettylou Cox
      Duchess
      Registered On: May 26, 2019
      Topics: 17
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      Yes, both times. For the first, I was 9 or 10, and my favorite playmates were twin girls, Norma and Naomi, who lived across the street. We would pretend to be movie characters, their favorite being Tarzan and Jane (which parts they took). That left me with “Boy”, only they re-wrote the script to make it “Girl”, and loaned me a dress for the part. Oddly enough, I don’t recall any “special” feelings from wearing the dress; that came later, during a brief Dressing episode while in my teens

      But the second time, Oh MY! About 7 years ago, a year after my bypass surgery, I was in my doctor’s office, discussing my difficulty with bringing my Cholesterol down; that I had even switched fro cow to Soy milk as part of my efforts. He replied that men shouldn’t consume Soy, because it can cause breast development. As soon as I returned home, I stripped to the waist and took a close look…and sure enough, I was growing a nice pair of girls. The revelation flipped a switch somewhere in my head, and I began buying ladies’s tees, a bra and a tee-shirt dress (which I wore when my wife was out with her friends—and Bettylou was re-born.

    • #423931
      Caty Ryan
      Baroness
      Registered On: August 27, 2017
      Topics: 71
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      My earliest memories of cross dressing are circa primary school days. There was a trunk full of women’s clothes in the garage of our home; I seem to remember enjoying getting the dresses out and putting them on. My Mother also had an old pair of bathers in our laundry and when she was not home, I’d go in there and try them on. “Worse still!!!” about that time, I found an encyclopedia article on women’s period dress quite fascinating, so I guess my love of wearing these clothes stems from that time.

      I can also clearly recall how beautiful my Mum looked when she and my father were attending a formal ball; I guess I wanted to look like her–all beautifully coiffed, perfumed, made up, and dressed in a long evening gown. (Perhaps that’s where my ongoing love of formal wear came from too!!)

      Moving to my early teens, my parents had a holiday cottage where, (though it would never be allowed these days), I refused to go for winter weekends, as there was “nothing to do”. So this gave me the chance to be on my own and dress in all my mother’s finery. (Tennis balls had to make do for breasts in one of her bras… But that was OK). I especially enjoyed the tightness of her panty girdles and feeling the tautness of the attached suspenders to her stockings.

      Visit Transgender Heaven

      This went on for some time, until, inevitably some relatives called in to check on me one night and I was well and truly “Sprung”. Being a typical “father of the age”, i.e. the 60’s, my father’s “severe talking to” about this “hobby” of mine, centered on the retribution I would face when I got older if the “boys in the pub” found out about my penchant for things feminine!!

      I attended a trade oriented, all male high school where drama and plays were hardly given a mention. So it can only be imagined how jealous I was when I read a newspaper article about how in the best tradition of all male private schools of the era, boys were selected to play the female roles in the school’s annual production. Males playing “Lady Bracknell” in the “Importance of Being Earnest” have had me green with envy ever since!!!!

      So that’s how it all started.Anyone wishing to follow on from the above only needs to go to my articles and photos in this site to see how far this, (now old “chook”, aka chicken), has progressed from demure bride/bridesmaid, through to “elegant middle aged mother of the bride/demurely dressed shopper and diner”

      “Aunt Caty”.

      As I am known by a “young thing” I met via this site and have mentored as my “Niece”…Its great to return the favour as I too was mentored by an “Aunt” in my earlier days…Even if she did live in Western Canada and I’m “down here”in Oz!!

       

       

      • #423975
        Leonara
        Ambassador
        Registered On: October 13, 2015
        Topics: 4
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        Thank you Caty… Great reply… Thanks for sharing
        Regards, Leonara

        4 users thanked author for this post.
        • #424012
          Caty Ryan
          Baroness
          Registered On: August 27, 2017
          Topics: 71
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          Hi Leonara,

          “Aw shucks it was nuthin”. All I did was copy and paste the first 1/4 of my CDH article on the same subject. Published on here circa 2 years ago..

          Happy New Year!!

          Caty

           

          1 user thanked author for this post.
    • #423891
      jennifer
      Lady
      Registered On: February 11, 2016
      Topics: 0
      Replies: 20
      Has thanked: 7 times
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      My mom gave me her nylons to put on to stay warmer in the winter and her high boots with small heals .they were great for sliding

    • #423875
      Stephanie Rose
      Duchess
      Registered On: December 26, 2020
      Topics: 3
      Replies: 2
      Has thanked: 6 times
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      I remember looking at the womens sections in the Sears and JC Penny catalogs. I grew up with two sisters and they always had items hanging in the bathroom. One day I was home alone and was in the bathroom and thinking about the pictures in the catalog, I looked up and saw the pantyhose hanging.  So naturally I decided I had to try them on.  The rest is history, I could not believe how they felt.  The next month my parents and sisters went off on vacation and I was home alone for the week.  This time I went all out, I shaved my legs and underarms then went into my sisters room. I rummaged her drawers and found a pair of matching panties and bra. I put them on and them put on the pantyhose.  WOW the felling on pantyhose on freshly shaven legs is totally amazing (if you have not done you must try).  I then found a dress and put in on,  My one sisters shoes were too small but checking my other sisters shoes they fit.  I looked in the mirror and felt this was right.  I dressed all week then washed and put away their things.   I was now hooked.  I dressed when I could and was depressed when I could not.

      Stephanie

    • #423848
      Laura Jane Moore
      Lady
      Registered On: July 10, 2020
      Topics: 3
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      I was 4 or 5, but definitely pre-school as my older brother was at school. I had seen a TV show, the Aldrich Family the night before and had a dream about a scene in the show where Henry Aldrich the young boy of the family was wearing a dress in a footrace.  In my dream, I was wearing the dress. I went to my mom’s lingerie drawer in the morning and fished out a girdle and stepped into  the much too large garment as my mother and grandmother passed by the room. They had a good laugh at my expense but didn’t realize this was the beginning of a lifelong love of all things feminine.

      5 users thanked author for this post.
    • #423836
      Celeste Starre
      Lady
      Registered On: June 26, 2018
      Topics: 31
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      Curiosity    I was home alone as my parents were gone for the weekend. I was 12 or 13.  I saw one of my mothers jacket dresses hanging in her room and wondered what it would be like to wear it.  This was the early 60’s when women went all out with hats gloves etc. and that first time I went all out.  Panty girdle&nylons,bra,slip,dress,hat,gloves,jewelry,purse,heels,and red lipstick. That was the beginning and I loved it. To this day I still love the 50’s look.

      • #423837
        Jessie Monroe
        Lady
        Registered On: December 27, 2020
        Topics: 0
        Replies: 23
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        Lovely story gf! Oh how I wish I was born a woman!

        1 user thanked author for this post.
    • #423829
      Jessie Monroe
      Lady
      Registered On: December 27, 2020
      Topics: 0
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      I remember like yesterday. My older sister had a maroon scoop neck shirt that really highlighted her cleavage. I fell in love with it, stole it and so much wanted to show my growing cleavage as I was slightly overweight and beginning to have gynecomastia. As soon as I put it on pushed up my developing breasts and saw what I realized was me (a femme cd) I was hooked! Next I stole a bikini of her, felt the nylon liner of the bottom and that I could fill out her top as well as her and realized I wanted to be a woman. I was 12 and 45 years later I am still that girl inside!

    • #423827
      Kelly Ann
      Duchess
      Registered On: November 7, 2020
      Topics: 1
      Replies: 17
      Has thanked: 0 times
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      Hi

      Rossydoo

      I remember it was my moms french knickers and cami sole and pantyhose and she had a lovely white blouse with frilled cuffs and coller and black pencil skirt I was forever trying them on even do they where to big on me

      She caught me one day and smiled and said don’t you look very pretty

      I then started wearing my sisters clothes as there was only a year between us and where the same size and my mom said they fitted me better than her clothes but that didn’t stop me wearing mom’s clothes and I think my mom knew I was different  and I’m still the same today

       

      L❤ve

      Kelly💋Ann

      • #423830
        Trisha Lilly Langdan
        Lady
        Registered On: December 8, 2020
        Topics: 18
        Replies: 285
        Has thanked: 2297 times
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        Hi Kelly, you mum sounds amazing. Not sure what my mum would have said if she caught me.

        Love Trish

        3 users thanked author for this post.
    • #423824
      Trisha Lilly Langdan
      Lady
      Registered On: December 8, 2020
      Topics: 18
      Replies: 285
      Has thanked: 2297 times
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      Hi Rosydoo, it was my sister’s fault, in a way. After my mum and dad’s wedding my sister left her dress hanging on the outside of my wardrobe. A love long purple think, we still have it I think. I wonder how I’d look in it now? Sorry back to the point. It say there staring at me for months, I think. Til on day I tried it on, when no one was looking. Tried it again afterwards this time got a pair of heels from some ware in the house. Clicked about in a dress that was too big and heels even bigger for my 12yo feet.

      Didn’t dress for nearly 15 years after that but I remember the satin feeling of that dress to this day. Should I revisited that dress I wonder?

      Love Trish

       

       

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    • #423821
      Stephanie Bass
      Princess - Annual
      Registered On: November 30, 2019
      Topics: 9
      Replies: 1065
      Has thanked: 9958 times
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      Hi Rosydoo nice to meet you  and when very young an older brother to busy with his friends to mess with a younger brother so it was me and a younger sister we played a lot together. As mom kind of helped push this  to play with sister with dolls and when no one else was there a little dressup time to make sister happy . Then young teenage years as mom knew she had a more of a girly son than not so for Halloween she sent brother and sister off to trick or treat with friends and ?? kept me home that day as a aunt showed up . They as mom and aunt  made me up as the pretty woman i thought i was anyhow  decked to the nines . All lingere dress heels  wig jewelry  and such pretty makeup i was a pretty girl  not the little boy that usually looked back from the mirror  that evening had a little time to walk around the house in the heels and practice  then we went to a different part of town so not to be outed   such a wonderful time in my life   . Pretty sure that was the start playing with sister and grew from there . really wish they would have taken pictures of that Halloween such a wonderful time in my girly life .

      Stephanie Bass

       

      • #425429
        Jessie Monroe
        Lady
        Registered On: December 27, 2020
        Topics: 0
        Replies: 23
        Has thanked: 7 times
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        Lovely story hon!

        2 users thanked author for this post.
      • #423822
        Rosydoo
        Duchess
        Registered On: July 15, 2016
        Topics: 1
        Replies: 4
        Has thanked: 26 times
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        Stephanie: I do actually have a photo of the event. Tried to upload it but it is my first photo upload. I think it has to be approved by a moderator or something and then should appear. I am lucky to have the photo.

        3 users thanked author for this post.
        • #423835
          Stephanie Bass
          Princess - Annual
          Registered On: November 30, 2019
          Topics: 9
          Replies: 1065
          Has thanked: 9958 times
          Been thanked: 3426 times

          Lucky girl you  so wish for this to have happened but dad and brother would not have approved  so mom didnt take any  maybe aunt but ?? lost track of her in the years   💞💋💋

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