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    • #698712
      Rosiebeth
      Lady

      For me.  I was 13.  Everyone was gone for the day.  I went to my moms room and I could no longer resist the urge to try my moms wedding dress on.   I pulled it and put it on the bed.  A 1950 style gown.  I pulled out the gift box with the wedding lingerie.  I put on the corset and panties.  Secured the hosiery.  I put on foundation, eye liner, mascara, eye shadow and powder.  I slipped into the gown.  I put on my moms short curly wig.  Found some Pearl clip ons and Pearl necklace.  Fake French nails.  I put on lipstick.  Since my dad passed away a few years early I put on my moms engagement ring and wedding band.  Then I slipped on her heels.   I was so excited my heart raced. I was so in heaven and so excited.   I’ve never stopped crossdressimg since that day. It define me and my love of wedding gowns.

    • #698716

      The day my wife disposed of the few remaining items of male clothing and she told me from that day forward I would be living my life as Jennifer Lynn

      • #699318
        Dawn Judson
        Ambassador

        I want to hear more about that, JL. That would be a dream come true for me. Your wife was OK with losing her man? How did friends & family react? Have you transitioned?

    • #698722

      Discovering and then trying on my mom’s romantic lingerie at 13. It was incredible to wear it and see how beautiful I looked in it and there was no going back at that point.

    • #698728

      I guess my defining moment was the first time I was out in public dressed and was called Mamme.

    • #698729

      The day mom dressed me in a bikini and wig for Halloween. I was about 5 or 6 yrs old . She had been dressing me in girls clothes for who knows how long , but it was.that day that I remember the most. Oh what a thrill it was to be in a bikini and only if she knew how that night would change me. Hugs, Allysa

       

    • #698742
      Anonymous

      Defining moment? Hmmm, well, for me I can’t say that there was one specific moment because I’ve been a crossdresser for as long as I can remember. My earliest memories as a young child are of playing with dolls and makeup and dressing up as a girl, and it’s only continued since then.I used to dress up in my mom’s lingerie an clothes, put on her makeup and heels and wig and jewelry when she was at work, and pretend that I was the woman of the house. But that was always confined to just being inside the house, so I couldn’t show the world who I really felt that I was.

      However, I would guess that if I had to pick one specific moment when I knew that crossdressing and presenting as a woman was 100% right for me, it would have to be the first time I ever fully feminized my body by shaving all my male hair (yuck!) off my body and for the first time experiencing what it really felt like to wear lingerie next to my skin that I could really feel and experience all those wonderful sensations. I was probably about 19 and living on my own when I did that. I dressed completely and totally as a young woman in lingerie, pantyhose, half slip, blouse, skirt, heels, with full makeup, a wig, I did my nails, wore pretty jewelry and spritzed on some light floral perfume. I was in a pink fog before I ever knew what the pink fog was! As I put my things in my purse and minced out to my car, I felt every inch the young woman I was presenting as, and it just felt totally and completely natural and right to be seen as a woman by everyone. That’s the first time I remember really and truly showing the world the woman I’ve always felt that I was inside, and it was wonderful!!

      Hugs,

      Holly

      • #698753
        Rosiebeth
        Lady

        Such an awesome feeling and experience.   Thanks for sharing.

    • #698755

      There has never been a defining moment for me since it was never a choice. It’s jus something I have always been since my earliest memories. I have been a closet crossdresser my entire life.

      Hugs,

      Michelle

    • #698763
      Caty Ryan
      Baroness

      I dressed in my mothers clothes from early teenage years, but I dont think my “defining moment” came until I had my first dressing service makeover in London UK in the late 80’s. Or perhaps my same era times of having my own second hand bridal gown and dressing in my hotel room on  interstate business trips.

      https://www.crossdresserheaven.com/photo/the-sydney-bride/

      https://www.crossdresserheaven.com/public-photos/?profile=Ryan%20Paul

      It just grew from there on, first time out in public in a shopping mall and “going to the ladies”. First time when fully dressed and made up in period evening gowns. First time at a CD Convention eg Seahorse NSW Ball, 2014

      https://www.crossdresserheaven.com/photo/scarlett-ocaty/

      https://www.crossdresserheaven.com/photo/lady-catherine-of-alphington/

      I nearly had an “attack of the vapors”, the first time I was made up and tried on that “Marie Antionette”gown.

      Another VERY special moment was the first time I tried on my “Gold Seal” attachable forms sans bra and had them “hanging” like a “real?? female. Properly tucked as well… of course…

      Oh and of course…. Earlier this year bra shopping en femme

      https://www.crossdresserheaven.com/photo/bra-fitting-x2-getting-professionally-fitted/

      So I guess too many “firsts for any to be a first”, but lovely memories all of them.

      Caty.

       

       

       

       

       

       

       

    • #698771
      Angela Booth
      Hostess

      About five years old putting on my sisters dress, that did it for me.

      • #698774
        Rosiebeth
        Lady

        I guess defining moment I should have clarified more.  I think all us girls started dressing at a very young age experimenting.  It wasn’t until I wore my moms wedding gown and pretending to be a bride that I realized who I am and that began defining who I was becoming.

    • #698783

      I have always felt that I should have been born female, and dreamt about being magically transformed into a girl before I was even five years old.  There are two moments, really, that stand out for me as far as crossdressing:  when I was six years old my older sister had outgrown her baby blue party dress, all frilly with full skirt and Juliet sleeves, and I somehow managed to get it and hid it in my closet.  When I was alone I would put it on and look in the mirror and I would be so happy wearing it.  My mother discovered it and after questioning me about it I never saw it again.  A decade later I managed to rescue from the trash one of my mother’s castoff bras and a sexy panty girdle, black, lacy, with sexy red trim, that had been my older sister’s.  I absolutely loved rolling the stockings up my legs and attaching the garters, putting on the bra with my home-made breast forms, and then putting on the red velvet floor length gown that I had somehow managed to sneak into the house after I had found it.  Those two moments pretty much sealed the deal for me.  There’s not a day gone by since then that I haven’t had crossdressing in my mind.

      • #739741

        Always a thrill to squeeze into a nice girdle, and attach silky stockings!

    • #698786
      Anonymous

      For me it was coming to the realization that I have to be true to myself after many starting and stoppings. I reach the point this year that I needed to stop being something I was not. Sharing this with my wife sealed the deal. No looking back now on this wonderful journey.

    • #698788
      DeLora
      Lady

      Interesting question, but for me I don’t think that such a moment exists. It was always a part of me even though it was a part that I hated for much of my life.

      Having figured out that I am transgender has made it much easier to accept, it all makes sense now! But even that realization only dawned on me slowly, there is no single tipping point. I guess I was always trans, right from early brain development in the second trimester so I am what I am!

    • #698789

      The defining moment for me was trying on one of my older sister’s prom dresses when I was 14. It was the first time I put on a dress and I couldn’t believe how amazing it looked on me.

    • #698795

      I think the day I put on my mothers bra and skirt and white blouse started my journey and then I discovered her high waisted girdles.I was in my own Crossdresser Heaven .I have been dressing ever since and have loved every minute of my journey.

    • #698796
      ChloeC
      Duchess

      Well, this is probably a little different than what some of the other responses were.  I mean, I asked my mother to make me a dress when I was like 4 or 5 and she did.  I remember specifically imagining (or daydreaming) myself as a female maybe around 9 or 10.  I remember vividly sneaking into my mother’s wardrobe and trying on shapewear and a dress somewhere between 12 and 15.

      But perhaps the defining moment came when my mother caught me and admonished me on the drawbacks and pitfalls and serious issues that I might face for being gay (she used the other word I really don’t care for).  I knew right then that I definitely wasn’t that and it probably spurred me on to determine exactly what I was.  I started seriously reading up, studying, etc. I knew I was different, but I wasn’t that.  The only alternative was either a cross-dresser (I also don’t care for that other word), a ‘shemale’ which is either more distasteful to me, or a hopeful transsexual. I figured I was at least a cross-dresser.

      Hugs, ChloëC

      • #698854

        So jealous, that must’ve been awesome to have a mom give loving help.

    • #698804

      when the transition from stockings to pantyhose happened, and my single parent mom decided to try them out, so from an apartment full of ladies attire for office work, pantyhose were introduced to the laundry basket and towel rack, instead of the old nylon stockings and corsets. and to my pleasure, I loved them, back then they where made of  100% nylon with very little stretch. so one afternoon after school while I was trying on different clothes, I was wearing a pair of queensize beige pantyhose, of course they were really loose on my legs and just sliding all over my whole body from my armpits down, I just had to jump around in these hose and  you guessed it….my time started all over these giant pantyhose, what a feeling in my head and my whole body shook, I knew from there what I enjoy and now, I know how to achieve it……thank you mom for the pantyhose!

    • #698807

      I had to be about 11 or so. My older sister was taking tap dancing classes, and I used to love to try on the costumes that were made for her recitals. Then came her confirmation in church. She wore a lovely white dress, and I tried that on a short time later along with a bra, panties, slip and stockings. I have been hooked ever since. That was nearly 60 years ago! XO – Julia

    • #698811
      Roberta Broussard
      Duchess - Annual

      I think my first moment came when I was perhaps 9 or 10. My mom had her one-piece swimsuit drying over the shower rod. I pulled it down and put it on. The suit hid my boy parts and the cups made me look like I had breast.  I suddenly felt like I found the real me.

      Out of shame and guilt I’ve kept these feeling hid all of my life. Sure, I would buy a few pieces of lingerie from time to time. It was not until two yrs. ago that I bought forms and hair along with a full set of clothes. Thats when my real awakening came. I was fully dressed and stood in the mirror with a woman looking back at me.  Thats when I realized what I could have been.

    • #698813

      Thought provoking topic.

      For me I started dressing when I was about 12 with my mothers things when I was home alone.  I don’t remember what started me doing that but I do remember I liked the feeling of wearing them.  Throughout my life between marriages I would dress, mostly in lingerie that was left behind by my ex’s.  There was one point where I bought myself panties, a skirt and blouse and would dress when home (I lived alone at the time) but when my parents were going to visit I purged out of fear of them finding my things.  About 3 years ago I wound up getting into a discussion with my wife which led to me admitting to liking wearing feminine clothing.  It hasn’t been easy but since that time Suzanne has come out of her box and, much to my delight, been able to enjoy the time she has to dress.  It is not that often and is done in the privacy of home when alone but just being able to be open and free to do so is amazing.

      XOXO
      Suzanne

    • #698823

      My defining moment was when I started buying my own female clothes. My wife was out of town for a week, and I had been contemplating working up the courage to shop for my own things. I recall that I was very nervous, even looking at things in Women’s departments at first. I would only go to stores with self check outs. At that time, buying on line wasn’t an option, since the delivery wouldn’t come fast enough. So, I bought some black tights. That went so well that I found a bra that I thought could fit. Eventually I got up enough nerve to buy a dress and check out with a cashier. It was closer to Christmas, and I reasoned that it would be easy to explain, if asked, that it was a present. But as is usually the case, the cashier didn’t say anything. But one thing that happened when checking out was that she held up the dress over her head for everyone behind me to see, while she laid it carefully on the counter to fold it. I don’t think anyone behind me thought anything of it, but needless to say,it was traumatic in my mind since that was the first time in a checkout line with a cashier.

      One other time comes to mind was when I visited a Payless shore store. They used to stock large sized Women’s shoes. I saw a pair of heels that were in my size, but I didn’t want to attract attention and in my mind hear anyone in the store saying or asking why a man was buying high heels. These were large sized heels, so it was obvious that they weren’t for any one but me. So, as a result, I first walked away, not having the nerve to buy them. I had never walked in heels before and it was always something I wanted to do. This was my chance since I am cursed with larger feet than most women, I decided to get some lunch and contemplate what I was going to do. During lunch I talked myself into going back and buying them since this would be my only chance at owning heels in my size. I went back and the store was virtually empty, and picked up the box and went to the check out. As I was checking out, 2 ladies walked in. Again for some reason, the cashier chose to lift up both shoes in the air so everyone could see what I was buying, I guess to verify that they were both the same size. I heard the 2 ladies break out into laughter as they walked past, but I never knew if they were laughing at the guy buying high heels or something else. I like to think it was something else, and as I have learned from reading here, I really shouldn’t care which it was.

      But after going through both of those cashier check outs where I was trying to be discreet, and hoped the items would be bagged as soon as possible, I decided that this was a defining moment in my crossdressing. If I was willing to endure what was, in my mind, those stressful moments, I for sure wasn’t going to be able to give up crossdressing.

      • #698873
        Tanya
        Lady

        It’s hard to come up with one defining moment because it’s been a long process but if I had to pick one it would be buying a pair of size 12 high heels at pay less shoes. Similar to your experience it was nerve wracking and exciting at the same time.  The cashier didn’t hold the shoes up but she did say to me “these are one of our most comfortable shoes”.  She knew they were for me, but I realized that I didn’t care. I had just brought myself my own pair of high heels and it felt great.

    • #698830

      For me, I remember dressing and gearing excited, and pleasuring myself and then I would very quickly get un dressed and put everything back in the hamper.  So I decided that I would try wearing the panties afterwords and see that felt like. Then the stockings stayed on the next time. Then the dress stayed on, then the clothes were put on and did not pleasure myself and this felt better than ever.  I was hooked.  It need my own clothes after that.  I found ways to buy thing and keep them.

      Now I only feel right in Panties and ladies wear.  I will never go back to the old clothes.  This is just so much more comfortable.

      Hugs Paula

    • #698833
      Janet Woodham
      Duchess - Annual

      In my teens my parents went on holiday, and I dressed one of mother’s dresses, slip bra and underwear together with wig and makeup.  I used socks as breast forms. I felt a sense of peace, went on doing this whenever I could. I also started to find boys attractive. Then I realised I liked girls too dealt with a lot of guilt until I “grew out” of dressing around 19, until my forties. Despite the long break this was what me set on my path.

    • #698838

      I love this, what a brave moment.

    • #698846

      I started dressing in my early teens but it really clicked when I was in my early twenties my wife borrowed a cute dress from her sister for a Christmas party all though she didn’t wear it due to it being too big but when I finally had the chance to try it on it was the first dress that fit me perfectly and I knew I was a crossdresser from that point on.

    • #698849
      Anonymous

      There have been a number of moments. Early childhood experience of wearing a slip, followed by wearing my sisters pantyhose as a teen. One indelible moment was slipping on my wife’s curly wig and catching a glimpse of myself in the mirror… I looked so much like a woman that I was shaken by the experience.

    • #698851

      For myself first time I went for a drive as full Charlotte so happy and comfy as Charlotte. Will be venturing out as Charlotte w3henever possible.

    • #698855
      MelanieElizabeth
      Ambassador

      My defining moment was related to the first time I fully dressed but didn’t exactly happed looking in the mirror that memorable day. It happened a few days later, looking at the pictures of myself and reminiscing about it. It was the day I accepted myself as a cross dresser and realized this was more than just a thing I did, it was a big part of who I am and will be moving forward in my life.
      This acceptance in my own head led me to do many things I never thought I would and all of them have affected my life in positive ways. It motivated me to tell my wife about what I had been going at least partially since childhood. It hasn’t been perfect but at least I’m no longer harboring this secret alone. It’s lead me to join cdh which has assisted me in more ways than I can say. I know I’m not alone anymore thanks to this community and the people I’ve met online as well as the fellow cds I’ve been lucky enough to meet in person. That realization and acceptance of it was my defining  moment as a cross dresser.

      • #698867
        Janet Woodham
        Duchess - Annual

        Thank you for sharing this Melanie.

    • #698874

      Like most of you girls I too had the same experience at 14 putting on my sisters clothes with bra and nylons and dress while home alone and was taken with all the excitement of being a girl. A few years later I stepped out to a drag event with a friend and was amazed how I was treated by all the admirers and gurls at the club. Other girls sharing makeup in the women’s bathroom and dancing with the admirers that night and being treated like a real girl.

    • #698875

      The moment that I went to renew my pilots license and the Examiner looked up and he said “can I help you ma’am”?  I was the only person in the office and had guy clothes and a guy haircut and suddenly realized that he was talking to me.  I had been misgendered before but finally realized that it wasn’t a joke or mistake.  People actually saw me as a woman and that if I was going to be seen that way I would become the best woman possible.  I knew that I had an intersex condition but never really embraced it until that moment.  That’s when I became  “Marg ! ” and the rest is history.  Thanks Rosiebeth for this interesting question.

      Marg Produe

    • #698876
      Anonymous
      Lady

      I can’t think of any defining moment because I’ve always wanted to wear feminine clothes and would go through what ever to obtain them.

      I remember back in the day those times standing in front of some cashier waiting nervously for them to ring up my bra feeling like it was taking forever. Embarrassed to death wishing time had not stopped and the female customer behind me would stop snickering. My ears burning a bright red with little sweat beads forming on my brow as I shakily held out my money for the slow as molasses clerk to take and end my misery. I always assumed they were torturing me on purpose. This man buying womens lingerie, so nervous it was obvious it was for the pervert himself! This pretty D cup bra looked like it would fit him just fine. With the clerk grinning like a mule eating briars, I was not even caring about the change but just wanting to flee out the door clutching my new lingerie like precious gold, which it was to me. I never ran marathons but felt I did standing in a checkout line. Yep, fun times. Its a wonder I never fainted or had a heart attack but it was always worth it. Sadly it was a cycle of acquiring, enjoying, purging, then repeat, over and over.

    • #698882
      Trish White
      Baroness

      Hi Rosie, this is an easy one for me. The defining moment for me was honestly when I was born. My earliest attraction to soft silky things was when I was 3 or 4. I found a pair of either shorts or panties and I used to sit and just rub my fingers over the material. It made me feel good just doing that. The rest of my journey was just an expansion of that moment that I’ve always remembered. Thanks for the post.

      Trish

    • #698917
      Sherri Remington
      Duchess - Annual

      I have three defining moments. First was, as most of us when I was 8 and sneaking at night into the hamper and wearing my older sisters bras and pantie girdle and loved the feeling. It wasn’t sexual because I didn’t know what sexual was at that age, it just felt really good. Second was Halloween when I was 9 and dressed as a girl and at one house the owner said ” well when I was a child we would dress up for Halloween.” I had to explain that I was a boy or she wasn’t going to give me any candy. And third was when without any fear, I walked into a department store, went into the women’s department and bought my first sexy matching bra and pantie set.

      So here I am 30 some years later and I love being Sherri when I can.

      Ssherri

      • #698918
        Sherri Remington
        Duchess - Annual

        That’s Sherri with one s not two, gees, I can’t sing my own name.

    • #698926

      For me it was the first time that I pulled on a pair of tights:  the smooth, snug feeling melded with the excitement of being “different” and made me realise that – THAT WAS IT!  Yes; there was a very definite “physical reaction” but that wasn’t what made it such a great experience – what made it for me was the realisation that this was ME!  This was how I wanted to be and what I knew deep down was the real me; I’m sure all the other ladies out there will be able to recognise what I’m talking about.  Holly XXX

    • #698927
      Emily Alt
      Managing Ambassador

      I think the deal was sealed the day I was born.

      The first sign occurred when I was 4.

      It was confirmed when I was 11.

    • #698946
      Fiona Black
      Baroness - Annual

      For me it was the first time I fully dressed as a woman. Cross dressing had been a lingerie fetish all my life until earlier this year when thoughts of dressing completely and going out in public became more predominant. I bought a few dresses, breast forms, wig and lipstick and the first time I put it all on and saw the woman looking back at me in the mirror was definitely my defining moment. I actually let out a soft “oh my” as an intense feeling of femininity washed over me. My entire life changed at that moment. I completely accepted myself as a cross dresser, no more hiding, no more shame. It also led to Fiona now comfortably spending time in public on average about five days per week. And I couldn’t be happier.

    • #698956

      I know now that I was born transgender, so the deal was sealed right then and there! That knowledge was with me throughout my life. I realize now that I was never crossdressing in female clothes, I was crossdressing in male clothes because the feminine clothes were what I was supposed to wear, and were what always felt natural.

      Hugs,

      Ms. Lauren M

    • #698979

      The girls (my cousins) painted my nails; I was three.  I was so happy.  Things changed, I wasn’t allowed to have red nail polish on.  I grew up with all girls.  I wanted to be pretty and soft too but there was never room for that.  I’d try their clothes on or my mothers knowing full well there would be hell to pay if they found a boy wanting to be be a girl.  I never got caught as far as I know.  The first time I tried pantyhose on I thought it was incredible—heaven— and I still do.  Actually, I absolutely love pantyhose.  Obviously, I wore their clothes, looked in the mirror and wanted nothing more to be one of them, a girl.  I never got caught got (everybody wanted a boy) but all I ever wanted was to be one of the girls.  Fortunately or unfortunately I was good at sports and as the cheerleaders cheered I just wanted to be one of them.  The skirts, the tights and jumping around.  Well, we had an opposite sex day during my senior year.  I loved my friend, Stacey, who dressed me up.  I lost my breath when I put on pantyhose (I still love it) but I had to go win a football game—we won.  I was so happy being a girl and then going to help us win.  Most people don’t get it and now women don’t wear pantyhose.  I tell my wife if you don’t wear pantyhose I will, she does.  How amazing life is to be a woman, I somewhat worship her.  And love is everything and she hates to know I dress up as a woman without her and I love it.  The clothes, skirts, silk blouses, high heels, slips, pantyhose, makeup, wigs, lipstick, the feel…and anyhow I do it privately.  This is the first time I’ve ever talked or wrote about it.

       

    • #698999
      Meredith
      Lady

      I was about 13, in junior high and had been admiring my classmates’ legs, they all wore short skirts and pantyhose.  I developed the strongest urge to be like them and my older sisters.  That summer I put on a pair of my mom’s pantyhose and was hooked.

    • #699020

      August 2022. I put on my first heels, ever, and felt sexy in a way I had never known.  With mens size 16 DDD feet since I was about 14 (ladies 20xw) there as never any possibility before I bought a pair to try it!

    • #699029
      Lola Caprice
      Baroness

      Even though I would try my Mom’s clothes on as an adolescent, and occasionally a few articles of my wife’s clothes on rare occasion as an adult, I did not think of myself as a crossdresser until my mid 50’s.  During the COVID lockdown in 2020 I was home alone a lot since my SO works in a hospital and I was working from home (kids are grown and gone).  I decided to settle a life long “curiosity” and buy some stockings and heels that fit me correctly.  My crossdressing evolved rapidly from there.  I made the excuse to myself that I could buy some lingerie and do a little dress-up floorshow for my SO to “spice things up” romantically.   The entire story of how that went is in my profile but to make it brief, by the time I got my outfit done, my little show together and my runway walk down, I knew there was no turning back.  I went through with the evening as planned but instead of it being a one-time thing as I originally intended, I ended up sitting down next to my SO in full Lola attire and telling her if she can’t accept me like this I understand and she will never see me dressed again but that I felt totally comfortable crossdressed and I would love to spend the entire evening together that way.  We had a beautiful evening together and that is when she gave me my femme name Lola.

    • #699055

      Well I have to say for as far as a defining moment from the very first time I tried on my sisters pantyhose I was instantly hooked for sure. But dressing back then was only when ever home alone. With all the struggles , guilt and shame I never wanted to admit that I may be a crossdresser even tho I found myself drawn to wearing femme things. So probably the moment I accepted myself and came out to my wife and said the words “Honey I’m a crossdresser “ Now I’m super proud to say these words as it’s a huge part of myself and only going further everyday with it.

    • #699087
      Anonymous
      Lady

      1. First a humorous moment – when I was little I was doing laundry with my mother and asked her what her bras were for and she explained that women wear them instead of undershirts.  Then in what could not have been a great moment for her, I asked her why her sisters have bigger breasts than her.  She said something along the lines of bigger breasts were beautiful and I declared that I hoped mine would be big.

      2. As a teenager, wearing mt mother’s bras and panties to school.

      3. Splurging on my own clothing for the first time, looking down and seeing my breast forms under my shirt and wearing heels.

    • #699097

      Oh my, I can’t single out moment that defined me as a CD.   However I’ll highlight a few moments that led me to this wonderful journey :

      – I was a latch key kid.  I had lots of time to myself in the house; one day I was exploring in my mom’s closet and found her purple one piece swimsuit (more of a swimdress) from Montgomery Ward (yeah it is that old).  I’ve worn my mom’s panties a few times but this swimsuit was entirely new.  I put it on and it was pure exhilarating.  The feel of soft smooth spandex against the skin was a new experience.   From that day forward, womens’ one piece swimsuit has been a big staple in Wendy’s wardrobe.

      – as I got older, I explored my mom’s closet even more.  She didn’t have very many dresses but I remember a long sleeved front button red dress that I loved wearing alot.  The fabric was silky smooth and felt wonderful.  She also had separates, some pencil style skirts and a few long sleeved blouses.  I edged towards the separates, and in part that is why today Wendy’s closet consists 99% of blouses and skirts.

      – I also got into my mom’s shapewear.  Unlike shapewear of today, it had actual rubber in it as you can smell the rubber on the material.   I loved the tightness of the shapewear, and wore her bra, cami, panty, and the shapewear when I dressed up in her separates.  I guess that is why today, I simply love shapewear.

       

       

       

       

    • #699130
      JOJO
      Lady

      My defining moment was when my mother had me dress as a Hawaiian Hula dancer for Halloween when I was young and I did not complain. The funny thing was that when I went trick or treating the neighbors said that I made a cute looking girl and that was it from then on.

    • #699134

      There are two moments that really stand out to me.

      The first came when I really fully committed to dressing up, rather than just sneaking a quick try on here and there. I bought a wig and a dress and heels and went to work in the evening all dressed up. No one was in the office at that time, and the sun had already gone down. There were a lot of people hanging around campus enjoying the cooler evening after the hot summer day. I was wearing a short, maroon office-style dress. After I finished work I decided to walk around campus a bit. Our library has these really big, mirror reflecting windows on the first floor and it’s a favorite place to go whenever I want to really see how I look at a distance. As I walked up the stairs to the library, I saw myself reflected in the windows and thought, wow, I really look good. I was so surprised at how natural and normal and comfortable I looked. I couldn’t help but smile, and that made me look even better. Sure, the light was soft and dark and forgiving, but it was still such a fun moment. I could watch myself as I walked past the library and it was so exhilarating and satisfying. I lost that dress in a purge and it’s one of the pieces I always wish I could get back. I bought another that I hoped would be similar, but it just isn’t quite the same That moment though, of seeing myself looking so good, has been foundational. Whenever I dress up, I’m always trying to capture that feeling again.

      Another key moment came after I had already dressed up several times at work, so it wasn’t a big deal being seen by coworkers. At the time, I shared an office with a lady and she needed to meet privately with one of her students, so I went down to a computer lab in the building to keep working. When I came back, she had gone and locked the door, and my purse and keys were inside. It wasn’t a big deal because the department secretary has keys for all the offices, but she wasn’t in either. In fact, nobody seemed to be anywhere in the department. It was a couple of hours walking around and talking to people before I figured out everyone was down on the quad at a corn hole tournament. I had to take my heels off and walk barefoot across the grass to find everyone. I have to say that barefoot walk across the grass, wearing my favorite office outfit and carrying my heels in my hand was one of the funnest, and sexiest feeling moments of my life. At that point, everyone in the department who hadn’t already seen me dressed now knew I liked to cross dress. A few explanations and everyone was accepting. No big deal. I got the keys and got back into my office, and went home. I always think about what a joy it was to be locked out and have to walk across that lawn.

    • #699135

      My defining moment when I was about 25. I was at a resale store and found a  beautiful dress in cobalt blue that fit me perfectly. I walked out of the dressing room and the proprietor said “Your going to drive the men crazy wearing that outfit”. She may have just been trying to make a sale but it is something I will never forget!

    • #699154
      Anonymous

      A few:

      1) when I was little, and I mean little, I would always put on this costume dress at one of my old baby sitters. At least until it no longer fit.

      2) my cousin made me wear an old dress of hers for a little homemade video one summer. She put make up on, breast forms, the whole thing. I was giddy as a school girl. Hehe

      3) one of my exes let me where the dress she wore to my command holiday party. It fit perfectly, and I loved wearing it. And some of the lingerie she bought while we were together.

      4) another ex and I shared clothes often as we were the same size.

       

    • #699222
      Edie Majeski
      Baroness

      I’ve been crossdressing for almost my entire life, having first dressed at a very young age of 5 or 6. For over forty years I was constantly told how indecent it is for a man to dress like a woman, thus I resisted the need to dress the best I could to make others happy. I was during those years I did most of my purging. Doesn’t take much to know how poorly my resisting went.

      It was in my forties that I got my first PC and connected with the internet. I spend hours on that PC trying to find an answer as to why I’m like this and if there was a way to stop. I guess you all know what I learned.

      It was at that point I did a complete turnaround. Instead of resisting, I embraced my need to dress, feeling: “why I should make myself miserable to make other happy”.  I then used that same PC to learn all I could to look my feminine best. Now nearly seventy, I’m still trying to lean even more to look my best.

      Edie

       

      • #699344

        Beautifully written…and can say proudly “same here”.

        My “career” started even before that.
        Much of that detail has been kept from me by a very well meaning older sister. Since I don’t have memories from before age 5, I presume ‘something’ happened. At a minimum, an imprint was made.

        Thank you!

        • #699448
          Krissy
          Lady

          Finding out that wearing lingerie is far more comfy than male pants plus I look amazing in a little black dress! But I think the most defining thing was removing all my body hair and living as a smoothie, once you become smooth you can never go back to being hairy, been a smoothie since 1987 now

      • #699352

        Edie, Your response here echoes my experience to a “T”. Well written and so right on for me too. 😉😊

    • #699284
      Julie
      Lady

      Seeing me in a dress while dressed in my Rachel cosplay but since she is a cosplay I prefer to dress as my female self Julie.

      • This reply was modified 1 year ago by Julie.
      • This reply was modified 1 year ago by Julie.
    • #699383
      Denise Little
      Duchess - Annual

      With kids gone from home, spouse working away from home and having the opportunity to work at home occasionally, I became curious to see how I would look dressed as a woman. One day I tried on my wife navy blue skirt, hosiery which I was scared to death to make a run in them with a pair of her dressed shoes that could fit me. A first look in the mirror revealed to me how good looking my legs were and how quickly I was adopting softer movements. This got me hooked in getting some clothes in my size through online shopping and searching on the internet to discover the word crossdressers and that I was not alone. This was 15 years ago while I was in my early 50’s. Now I understand better why I enjoyed listening and participating in girls talks.

    • #699451
      Anonymous
      Lady

      For me it was when I tried on my girlfriend clothes for the first time after sorting the washing out and got abit curious

      the defining moment was when I bought my own clothes and makeup it then became an obsession and then further defining moments occurred such as buying breasts,hip and bum defining underwear and full “ Jem up” whenever I can

      looking at myself in the mirror defines what I am and I love it

      Hugs

      Jem

       

    • #699452

      For me, finally giving in to impulse. I had no CD experiences as a child or teen, but  after marriage at 28 did sneakily try on some of my wife’s clothes for a time. Not liking the sneakiness and deciding it was over the top, I laid off off for 30 years or more.  In 2021, my wife was called out of town for a few days. I decided to explore my proclivity at that time, and acquired a few items of my own – pantyhose, panties, an inexpensive pair of heels and a kimono robe. The fact that they were my own things seemed to make a big difference.When I put them on, I experienced the sensual, euphoric sensations I had heard about and read about in forums like this. By the time my wife returned, I knew I was a crossdresser and there would be no turning back. I told my wife right away, she did not recoil in horror and was accepting.”Kris Burton” would emerge shortly thereafter.

    • #699458

      I was in my mid fifties. After my second purge I couldn’t resist fully embracing that side of me. As I restocked my wigs makeup and wardrobe I knew I would never quit. Nor did I want to. I excepted and embraced that side of me and will never look back.

    • #700764

      I think defining moments are when we stop grabbing an hour here and there trying on panties and buy our own stash, the wig, make up, nails, dresses, lingerie and heels etc and dress for a whole day or so. At least that’s what it was for me , from there,  it was no going back and i was hooked.

    • #700782

      Over the years much like many of you I have dabbled in crossdressing  mostly trying on my sisters stuff when no one was around.  Then later some of my wife’s thing when she wasn’t home.   It was not until I decided to take it further on a trip out of town for work that I really went down the rabbit hole.   I had a work trip to Tampa coming up so the plans commenced.  I booked a full body waxing on the first day and then a makeover the next day.   The waxing albeit a little painful was not too bad for never having any waxing done before.  BUT the FEELING. OMG!!!  The smoothness was euphoric to say the least.    I had gone shopping before the waxing session.  I slipped on some satin night wear and stockings.   I was in heaven.    Best night of my life or so I thought.   The next morning I woke up and prepared to go to my makeover (you know shave the face and moisturize). Showed up to my makeover shaking all over from being so nervous.  I was quickly calmed down and welcomed and treated like the lady I was meant to be.  I was pampered and shown how good you can feel in your own skin.  The makeover was the best experience to date.  The moment I was given the lingerie and breast forms. I knew I was hooked.   The feeling of having breasts was phenomenal. The look that the corset accomplished on my waist was also unparalleled.  I actually looked feminine. The feeling of the pantyhose and the makeup on my face along with the wig on my head all felt overwhelmingly emotional.  I was becoming me. When she turned me around to the mirror, my jaw dropped.  I did not recognize the beautiful woman staring back at me.   At that moment I saw my true authentic self staring back at me.  I then slipped on some four inch heels and began taking pictures.   Such a great experience.  After all of the the lady took me out to lunch as Ginger for the first time out in public en femme.   I was nervous but so excited!!! After lunch we went shopping for some things (dresses, heels, purse) for an evening out with another girl from this site.   The dinner went great and after that I went out to a club as myself too.   This was the best day and night of my life.     I went out each night that week as myself.  I can say that I have lived life to the fullest.
      hugs and kisses Ginger.

    • #700939
      Anonymous

      Like many of us, I had known from an early age that I wanted to dress as a girl. But, despite the familiar story of sneaking into mothers / sisters clothes during my teens, I didn’t have my first full taste of crossdressing until my 20s.

      At the time, my first wife had left but left me alone in our house – with a ton of her unwanted clothes. I slept in a nightie most nights and soon began dressing fully. One evening, I put on a luxurious blue satin dress with a black satin bodysuit underneath and sneaked into the garden under cover of darkness. I sat on the patio for an hour or so and it just felt so natural to be dressed this way.

      I think that’s when I realised that this was more of a need than a passing phase.

    • #701853

      My moment wasn’t until I got with a g/f who was basically a nympho, who was unashamed about her sexuality or her reputation. I actually fell in love with her on my first hello at 16 years old and she was 19, we became very firm and close friends up until I was in my early 30s about 33 and she would be 36-37, being a cocky little geezer from London who believed he knew absolutely everything about sex life relationships, well I found out how wrong I was. After a few months together with sex being xxxxxx rated and learning more about myself and all types of sex I was ask what she could do for me to really turn me on and being a bloke I said wear your kit stockings sissies heels etc, after a few times of her wearing this I found she was withdrawn quiet and I ask outright what a matter basically I’m bored I need you to do something for me and I ask what now this woman has opened me up I’ve no fear about anything sexual as she is leading me she ask me to wear stockings her heels suspender belt undies wig I did and I have never looked back in the moment of standing in front of her pass my intital embarrassment, the look she gave me of pure sex lust and filth, that was it I wore that and other stuff very regularly for her and enjoyed every moment, my dressing stopped for a while until 6 years ago when I was caught in my next gf undies and was surprised by the outcome with her uncle but that’s another story. I dress regularly now it’s a big part of my life I love being Janie and enjoy all the trappings of being a female for a few hours and also the power to watch a guy get very turned on by my dressing I love it best thing I have ever done

      • #721963
        Krissy
        Lady

        I think a girl can have so many ‘defining moments like 1st time buying from a lingerie section in a shop, 1st time you dress fully as a female, 1st time sexually and the list goes on! But for myself I think mine was around 3years ago when I finally realised that it’s not a phase or a kink, I really do look and feel much better as a women than I do as a man and over time I come to not like the male bits I can’t hide and want rid of the I.e body hair, male shape and the obvious bit in my dress that serves no function and I hate it.  So I can say if I had the money I would be straight in for the operations to make me as femme as I can as I’m so unhappy when I see it or any body hair that grows back and have started saving for the life changing things I’m going to have to do and I can’t wait to be as perfect as I can be as the women I should of born as xx

        Ss

         

    • #702109

      I had dressed in my mom’s pantyhose at the age of 4 so had years of experience but the defining aha! moment for me came much later in my late forties. I had hibernated for years and then it began innocently enough when I started to use Spanx tights for skiing as I have always wanted extremely thin socks for my ski boots and I thought they would act as a compression ‘tight’ for my thighs as well. But from the moment I put them on the flood of emotions that came back to me were overpowering. After that I “began again” and built a wardrobe. For the first time wanted to really work at makeup. What really shook me to my foundations were the girls who could really transform. I had never thought it was even possible but when I found so many examples on the web it became an obsession to see if I could pull it off. From there I began to buy everything. Makeup (so much makeup!) makeup bags, wigs, dresses, stockings, pantyhose, tights, leggings, lingerie, high heels (O my god I love high heels!) bras, panties, gaffs, breast inserts, jewelry, fake nails, fake eyelashes (I’ll never be the same after putting on fake eyelashes!), skirts, corsets!!!, blouses, etc. etc. I watched literally hundreds of how to’ makeup videos and transformation videos. Then I began to work at doing my makeup on any day I could dress and then photograph myself over and over to see how I looked. It was an overwhelming experience.

      But the day that was truly a defining moment came when after countless hours working on my makeup routine I finally had a total breakthrough in May 2018. I looked in the mirror one day and literally saw someone completely different from myself in the mirror. Felicia was truly staring back at me. Something shattered. It blew the doors completely off the hinges for me. It was a truly emotional experience. It made me so happy to see the woman inside finally get to take the stage. It really is unexplainable. That moment took my breath away and profoundly reshaped my inner landscape and it continues to do so daily.

    • #702326
      Anonymous

      When I go up in heels, magic happens

      • #703044
        Krissy
        Lady

        I find it way more easier to walk in heels and when i slip a pair on its heaven as i feel awesome and all woman x

      • #707256
        Krissy
        Lady

        I’ve had a good think about this question and I think there are so many in my case! I.e like the 1st time I bought ladies clothing and said to the assistant ” yes its for myself and I can’t wait to get into that dress, lingerie etc. As when I 1st started I had no idea what size I was? It was pot luck! Eventually I got my sizes and no more mistakes as can remember buying this beautiful dress and it was too small! Gutted as I ripped it trying to slide into it. So I chatted to a girl who i knew and was roughly my size as I knew 100% she was as i lent her a pair of jeans one night and they fitted her perfectly. Gosh so many defining moments the earliest ones were the best and sometimes the funniest..

        1

         

        • #707529
          Krissy
          Lady

          It was so liberating buying lingerie for the 1st time back in the 80s and you have to remember it wasn’t so good to be a different person back then as you would get lots of quiet giggles and whispering amongst the shop staff, although the next time I went into this shop they were straight over to Me when I swept into the lingerie section and eventually were really cool as I would like to try things on or at very least go in the changing rooms and see how it looked. Nowadays it’s your just another customer whether you male,female,trans or whatever gender or role you are that day. We have come such a long way x

    • #703043
      Krissy
      Lady

      For me it was when with a little bit of padding here and there, i looked better as a female than i did as a male and female clothes seem to fit me better than male clothes! That gave me a real high and back then it was a secret thing as nobody knew or suspected that i was born to wear womens clothes and they looked really good on me and with a little bit of work and a tad of make up i was very convincing in fact id get chatted up most Friday nights by hetro males who had no idea, id just play the aloof hard to get card and get bought drinks all night and they would be asking for a kiss and a snog never knowing i was born a male, i once kissed a boy on a bus and he was besotted with me and i had to tell him im not like most girls? I didn’t get the reponse i wanted and he felt cheated that i hadnt told him so from then on i played hard to get as i didnt want my secret to be told and not being passionate was the easy way out. It was heartbreaking as i met a girl and she wanted to have a lesbian relationship but i couldnt as i had that thing i was born with and when i finally told her i was heartbroken as i really loved her like a woman loves a woman. She was going to wait for me to have the op but she died of a drugs overdose and it sent me on a downward spiral and i slipped into drugs and drinking and it took many years to climb out of that hole. Still happier now and no regrets 2023 is going to be a year of change and it will be for the better as i know what i have to do. Merry Xmas and a happy new year girlfriends xx

    • #703056

      Oh Rosiebeth! I was tingling as you described dressing in your mom’s wedding dress! The thrill must have been indescribable! I hope you had more than one chance to do that. the butterflies in your stomach, the weakness in your knees, the incredible pink fog, the total joy! I am getting worked up here as I type. Imagine having pictures! Imagine having a video! Imagine walking down the aisle! Imagine having a special gurlfriend, dressing the same, right beside you! I am breathless with excitement from your story. Aren’t we unbelievably lucky to be gurls!

    • #703224
      J J
      Lady

      My defining moment was when I just realized the reason I dress en femme is because I enjoy it. That’s it, after years of wondering why I did this, going through all the various options and reasons, all of which play some part, I just accepted the fact that I enjoy putting on femme things.

      Yes there is an erotic aspect, yes there is a taboo part that excites, yes silk and satin feel good against my body, but none of those are in themselves the reason. I just enjoy the look and feel of dressing en femme.

    • #703677
      Amy Oxley
      Lady

      Not sure what age I was but must have been quite young. I was cast as a shepherd in the Nativity play at school and my costume robe was basically a long gown. The first moment I tried it on and felt it drop over my body I felt a tingle of excitement. Standing in front of all the other kids feeling great in my “dress”. From that moment on I was always more interested it girls clothes and it wasn’t long before I was trying on my mother’s things.

      • #706733
        Susan Zed
        Lady

        Its strange how “the fever” justs grabs us isnt it?

        • #739918

          There’d been moments on the way: my sister’s knickers and birthday frock, the entice of, and hint of slip, of the school secretarily staff.  My dropped pencil, half hooked!  At least for slips.  Then, later, trying on that floral empanelled panty girdle of my mother’s, hooked.

          • #739928
            Gail
            Lady

            I just adore Pantygirdles with garters attached to my sheer stockings.

            I used to watch TV growing up and being envious of the girls wearing Pretty Dresses with cute Petticoats. That was IT for me–I was only 5 at the time.

    • #703918

      My defining moment? Well, i think i was about 12 years old when I gave into the urge to try on my mother’s panties. But a few years later, I was hitchhiking and a guy gave me a ride. He kept hinting about sex and I just wanted to show somebody about Denise. So, I went home and put on my bra and panties that i kept hidden from my parents. Went back out to meet up with Bill. By the way, it was dark out so I was pretty safe from being seen by the neighbors. Anyway, Bill liked how I looked and kept saying so and hugging me. I felt so wonderfully feminine. I wanted that feeling all the time. All that closeness led to sex but that’s another story. (Grin). It was only that one time that I was with Bill and I missed it after that. It sealed the deal for me to become Denise as much as I could and I would not want to change the past in any way.

      Denise

    • #703935
      J J
      Lady

      In hindsight, I supposed it was the first time I dressed, but at the time it was not a defining moment, just something to do.

      I was borderline puberty, and one day just decided to try on one of my mothers outfits. I went all in, stuffed bra, panties girdle with garters and stockings, dress and a wig. I had never thought about dressing before, and other then one other time did not dress, nor even have a desire to dress for many years. It was just and one, or actually, two-off. What was defining was I got so excited I had my first ejaculation, so there was something special about dressing that I just didn’t realize at the time.

      I didn’t even think about putting on anything femme for many years, and a series of girlfriends, though I always did like their lingerie. Then, one day at random I put on my wife’s panties, enjoyed them immensely, but even then I didn’t start dressing for several more years and it was only to wear her panties, and then bras in bed together. I slowly widened my horizon by wearing new and different things until I realized I guess I am a crossdresser. I struggled a bit with it, but not much really, until I just accepted the fact I like to wear femme, hence why my defining moment is when I just accepted dressing en femme as part of me and that I enjoy it.

    • #704005
      Peggy Sue Williams
      Duchess - Annual

      This is always an interesting topic.

      Like many of us, I started out very early and was very fortunate to be mentored by two older girls who lived across the street from me.  By age five, I was dressing completely as a girl, with the knowledge of my mother.  Moreover, I had gone out in public dressed as a little girl with either my mother or the two girls who were mentoring me.

      As far as a defining moment goes, like many boys my age, when I was eight y.o., I joined the cub scouts.  The cub scouts were continually putting on various plays and skits for fund raisers that required the boys to play the parts of girls, and my mother always made sure I played the part of a girl, which I was very good at.  There I met a boy, about a year older than me, who had developed his own special female character named “Eloise,” whom he had perfected into an excellent little female entertainer.  I befriended him and learned all I could from him about becoming a female.  He was very talented and willing to share all that he knew.  I believe that was a defining moment for me, because there was no turning back for me, once I was exposed to his dedication to being a female, his wardrobe, female attitude, etc.

      I asked the two girls who were my neighbors that were my mentors if they would work with me on a few more areas that would help make me a better female, and as always, they were helpful.  My mother also allowed me a little space in our home to set up a small private area for my girl things, like the boy who played “Eloise” had, and she agreed.

      These early years were good, but rough years lay ahead.

    • #706594
      Susan Zed
      Lady

      When I was around five years old I found a bag of my Mom’s panties under her bed and tried a few pairs on. I liked a flowery silky pair which felt good to wear but thougt I would get into trouble if caught so took them off and didnt dress for about 6 years.Then one day when our parents were out my Sister asked if I wanted to wear a lacey party dress of hers for a game we were playing and I thought why not. I liked the feel of it and the long white socks she dressed me in and then she asked if I wanted to wear some of her knickers. I thought why not again. It was when I put them on and could feel the cool air going up to her knickers I was wearing and the feel of the dress on my legs that I suddenly felt excited and wonderful and hated taking them off. From then on I tried all sorts of ways to get my Sister to dress me and then like so many of us I ended up sneaking hers and my Mom’s clothes to my room to dress in secret. My Sister was great in helping me dress. For a long time I was too young to understand the feelings I was having until the first time I climaxed and I was wearing some of my Sister’s silky knickers, a skirt and socks like that first time. I felt so dirty and guilty as I had been brought up in a strict religous way and I told myself I would never ever do that again…which lasted about a week until I got hold of another pair of panties to “borrow”. That first time with the dress though was the defining moment.

      • This reply was modified 1 year ago by Susan Zed.
    • #706737

      When I saw the new PE kit for girls at my school and knew I had to have one of my own.  A gold polo shirt, navy blue gym knickers with two gold stripes down either side and a navy blue netball skirt.

      I borrowed my sisters when there was no-one around and later plucked up the courage to go and buy my own. I absolutely loved wearing it.

    • #707266
      Krissy
      Lady

      3things got me hooked when i 1st started off, shiny tights or stockings, sparkly dresses and high heels as once i mastered walking in them i knew id never be the same or go back. Oh and having a smooth body as its hard work at 1st all the hair removal as i was a real hairy male once but as soon as i hit puberty it all had to be removed as i wanted to look and be a woman as much as i could. Its funny how after all these years its when i wear male clothes i feel weird as alway felt at home in the female world and that helps too.

    • #718683

      My defining moment was when my sister and her friend took me to a party and introduced me as a “cousin”.  They did my make up and dressed me in a short club dress and heels.  It was the first time I shaved my whole body.  They put fake nails on me and painted them a pretty pink.  They had been mentoring me for months on feminine mannerisms and how to walk in heels.  I got so much attention I was overwhelmed.  At that point I was hooked.  I think I was 14 or 15   at that point but I had been crossdressing since I was 10.

    • #722218

      I’ve mentioned many times what my “crossdressing” defining moment is and I have it written on my profile page: When I was 8 or 9 years old and I asked my Grand Aunt if I could try on 3 pairs of nylon panties I found in her spare bedroom dresser.

      It “sparked” something that has remained a part of me ever since and since 2016 I have realized that I have a dominant feminine spirit and that I am gender fluid. My daily domestic “male” life doesn’t allow me to “crossdress” as much as I want to; and my want has gotten me into “hot water” a couple of times. However my evolved understanding and opportunities as an adult has lead me to fully express myself as a woman more than just trying on women’s clothes when I was a child.

    • #722224
      Dani
      Lady

      I started dressing at a young age. My mother wore those full slips with the cups in them. It was the 60’s and they were silky and satiny. I fell in love with it. I’ve always been chubby and I have always been crazy about boobs – even my own. All my life I have dressed. But I thought it was just an anomaly. I was sure I was the only one that did this and I always carried tremendous guilt. But I just couldn’t rid myself of this “scourge”. Then I discovered I was a cross dresser. And there were a lot of CD’s out there very much like me. I think that’s when the defining moment happened. I was finally free of that guilt and I wasn’t alone anymore.

      • #739713

        Dani,

        Wasn’t it a wonderful relief to discover you weren’t the only one?!? Just discovering that there were others out there just like me was a relief in itself. But after reading so many bios and posts on here, as well as help from my wife, I ditched the guilt like a bad habit. I’m glad you’re not alone anymore!

        Hugs, Jill

    • #738551

      in the mid-1970s, i tried on some of mom’s underwear: bra, panties, hose, slip.  i must have been 10or11years old.   i was inspired by the ads for Frederick’s of Hollywood in her Cosmo mag.

    • #739673
      Krissy
      Lady

      Ive spoken to many people and i think its down to that 1st time you dressed and for some its a bit strange
      And they never do it again
      But for many once you slip into female lingerie and a dress it feels like home and thats because it is! I never felt at home in male mode and felt comfy and at home dressing as a female and have always known its the way and only way im happy 😊

    • #739691
      J J
      Lady

      Thinking back on it a bit, it was probably the day my wife said they are just clothes when I told her I liked wearing panties, and most importantly that she was fine with it. I think it was then that I realized that I did like to wear lingerie and that she basically said she was fine with it so I started wearing panties more and more and soon exclusively. Bras and other lingerie soon followed and then dresses and the like, and she has always been fine about it. She would be just as happy if I didn’t, be she knows I enjoy it, and she likes seeing happy and does a nice job of pleasing me when I do wear femme things. She certainly jas done or said anything to discourage me.

      • #739900
        Krissy
        Lady

        Think there can be many defining moments,so recently ive gone past the tipping point where i actually own more femme clothes than male. When you get up in the morning and one automatically pull on knickers and bra and dont bat a eyelid as its the normal way to be. Just have one thing to remove and ill be at the destination ive been heading to since many many years ago, nobody can make me stop as its the goal ive wanted and im totally living day in day out as the woman i want to be. Rather look as beautiful as i can than live a lie as ive done that before and it chewed me up but happy times are here always

    • #739693
      Lucy Lace
      Lady

      I WAS 11 and was handed a lot of underwear by my sister (who always knews) and she said these are for you Lucy, get them on and lets go out to play.

    • #739711
      Anonymous

      Very similar for me.  I used to sneak in my moms walk in closet starting around age 7-8 and would put on whatever came close to fitting.  I never stopped dressing after that albeit secretly for most my life.

    • #739913

      I’ve always wanted to try on a wedding gown. There is a thrift shop near me where I have bought many femme things and I know they know they are for me as mostly I will try them on; they don’t bat an eye lid. They have several lovely white wedding dresses but I have never had the courage to ask if they are my size (they are hanging up on a wall out of my reach) and if so try one on. Their changing “room” (really a small space in a corner with a curtain) is too small to even put the dress on with the curtain closed and certainly not big enough that I can see how I look so I would have to step out of the room and use the mirror. I think I am going to pluck up courage and ask next time I am there. If I go in the week early AM I am nearly always the only customer. Another reason I hesitate is that I have no intention of buying one as I would not, I think, wear it at home, and it takes up so much room and would be easily seen by family visitors. Courage Marlene, you can do it. Best, Marlene.

    • #739951

      Buying my first wig, breast forms, and shaving off my mustache. I looked in the mirror, saw how beautiful I was, and knew I could not go back. And at 69, and not able to dress as often as I used to, as often as I’d like, I am still beautiful.

    • #740003

      While complaining about something I’ve long since forgotten, my wife told me to put on my big girl panties and deal with it.  I immediately recalled my young teen days (13 – 15) when I would try on my mom’s bras and girdles on the rare occasions I was home alone (I have 2 brothers).  I went out within 2 or 3 days and bought 2 pair of panties.  It took about 2 months for me to determine lace hipster panties are my preference and I’ve never looked back.  This was 3 years ago at age 74.  I’m a late bloomer.  My wife accepts I CD but neither participates or encourages me.

      I always wear lace panties.  Since 1/1/22, I have gone to bed wearing stockings, panties, a bra, DD forms, and a nightie.  I recently bought EE/F teardrop forms and an F cup lace bra that I wear to bed about half the time.  I generally change into fem mode (less makeup and wig) in the early evening.  After my wife heads to bed, on goes the wig, lipstick, and jewelry.  I remove the wig and jewelry before I go to bed.  Tonight, I actually put on press-on nails that I will remove in the morning.

      Anyway, I guess the defining moment was when I bought those first 2 pair of panties.  One they were worn, there was no turning back.  All I could do was refine what I was doing.

    • #740241

      The time that I knew I was different I was five years old. Of course I didn’t know anything about crossdressing but something stirred in me. I know I was kindergarten age and at that time only went to school in the afternoon. My older sister was playing with an old lipstick tube our mom gave her. It still had a bit of lipstick in it. She must have put some on herself. I was so drawn to it. Just the way I felt I already knew that it was a way that I shouldn’t. I don’t think I put any on my lips but I got a bunch on my hands. I didn’t get it all cleaned off but thought, know big deal. When I got on the bus on of the other girls noticed it right away. She accused me of playing with lipstick. I was so embarrassed I could have died. I was so self conscious about it knowing I was drawn to anything girly. Pantyhose was another big draw. Couldn’t wait for the day to get into some of those. That’s another story. So here I am now, full fledged crossdresser

    • #744715
      Anonymous
      Lady

      Mine was not at all glamorous but highly significant.I’d been a CD all my life without full understanding. it was the 1970s after all lol.

      One December evening when I was in my mid teens my parents went to watch my sister play in a concert. Not my scene so I was left at home.
      i immediately raided my mums wardrobe as soon as they left. underwear , panty hose , skirt , blouse, jumper , everything . it felt great.At that age I was almost identical in size to my mum including footwear .

      One task I’d been left to do was walk our beloved dog. So…….On went a casual hooded coat of hers with a pretty scarf and a pair of knee high boots. Off we went.

      Both the dog and I were happy that evening. He with his hour plus walk and me with the experience and the no going back feeling that instilled. Not least not even having sore feet after walking in block heels 😎

    • #744727

      slipping into my wife’s bra at age 62, brought back some memories of playing with moms things.  Once I put it on it felt so right and I knew I wanted to dress.  Realized how I had been repressing my fem side for so long and it was time to come to terms with stephanie.  Came out to my wife a few weeks later and now dress somewhat on a daily basis.

    • #744728

      My defining moment was in my early teens. Although I’d been dressed as a small boy in some of my sisters more unisex hand-me-downs (and I remember it felt good) and one summer my sister dressed me up as her sister a few times (and that felt good too), it was not really until I was a young teenager that I know my true self.

      My sister who is a few years older than me had just purchased some heels. When she brought them home and showed them to the rest of the family, all I could think about how jealous I was and that I need to try them on. A few days later the chance came. Everyone was out, I crept into her room, found the shoes and a flowy summer dress, some panties and a bra. And once the clothes were on, I know who I was – the term, I found out later, was a crossdresser. Although I knew it was ‘wrong’ to dress and I needed to hide it, I did not feel any shame, it was too right to be shameful.

      From that moment the motivation to dress was strong, persistent and constant.

    • #744771
      Staci Gal
      Lady

      I caught the CD bug late in life (but I always had a fem side).  On a hot summer day about six years ago, I was out in a t-shirt and jeans, drab mode. I was hot, uncomfortable and tired.
      I saw a gal out wearing a cute flowy midi dress and strappy flat sandals. She looked happy, comfy and wonderful, unlike how I felt.
      Then it came to me, I can do that too!
      Within the week I found a simple midi “LBD” and some kitten heels.
      Now I was that lady out in MY cute flowy dress and sandals.
      That was my defining moment and I have never looked back. I can do this!!

      Staci

    • #744781

      The heart-racing thrill of trying on my sister’s and mother’s bras and knickers as I was undergoing puberty. It felt lovely and right. I had forgotten those secret moments until recently, realizing that my yearnings for female identity go back to my transitioning from a child to a teenager.

      No wedding dresses in our house back then. Yours is a beautiful memory!

    • #744888

      Jr. High age, my mom’s panties…they were just part of trying on a full set of undies but those panties were the deal sealers. Knowing wearing her stuff would get me caught I took steps to acquire my own.

    • #754321

      My introduction to crossdressing started simple enough by basically modeling a dress for my wife that she was working on. And all my experiences crossdressing were with her. I always acted like I was just doing it for her, but I’m not a great actor and she wasn’t dumb. It was obvious how much I enjoyed it from the moment I tried on my first dress. Over the next couple yrs we’d push it farther and farther until I even had a few things of my own. We were more like “besties” on these nights, painting nails, trying stuff on, and I’d play with her hair. In those moments, I always enjoyed it….but, sometimes the day after I’d question myself? Is this right? Is this some sorta phase? Coming from a conservative background, I wasn’t supposed to enjoy these things. But, ultimately our marriage came to a quick end(unrelated to cd) and after she was gone, I REALLY questioned myself and over analyzed everything and sometimes I’d try to trace it back to those “girls nights” we had. I didn’t dress at all for about a year. I’d look at those clothes in the closet and get mad. But, then one evening after stressful day at work, I remembered that first time and how good it felt. I ran a bath, shaved my legs, and put on my favorite dress. That was my defining moment. When I finally accepted that this is just part of who I am. I was actually creating more anxiety for myself by trying to suppress these feelings.

    • #756750
      Janine
      Lady

      I had been dressing, as a girl since I was about 12 years old. I loved the way that lingerie feels on my body and the way that I look wearing stockings and a garter belt with 3 inch heels. Although I enjoyed the way that I looked and felt, there was something missing from the feeling of being feminine. My defining moment that convinced me that I am a crossdresser was when I sent away for a prosthetic vagina and couldn’t wait until it arrived at my house. As soon as I pull it on, I knew that this was the one thing  that was missing. I immediately felt so feminine and girly standing there in front of a mirror wearing a pair of suntan thigh high stocking and a garter belt holding them up and I knew that I looked more like a girl then I ever had I was hooked and I knew it

       

    • #756842

      I had been underdressing and some lingerie for over 20 years.. but the defining moment for me was getting a makeover and putting the wig on for the first time.. right there i knew that it was not a fetish, I truly fell in love with myself in that moment.. Something I have not felt about myself for a very long time.

      Xx Alexis

      • #756855

        This would be my experience EXACTLY. Lots of piece-wise dressing my whole life. Felt more like a fetish for feminine silky things. Finally made a full makeover happen at a studio and boom, the moment I looked in the mirror, it was like meeting myself for the first time? Hard to explain. But I saw a real person, someone who I’d felt for years, come to life.
        and I cried….. haha.

    • #756868

      Wow RosieBeth, you not6 only secretly came out of the closet…. but you Kicked Down The Door

      Meghan B.

    • #760360

      Like most everyone I started dressing early on and only in private. I was afraid to venture out in public. But as time went on I continually improved my look and really got the desire to go out. So I started to go out and found I was pretty passable and was getting attention from guys. So I started to really get the urge to date. So the defining moment for me was when I went out on my first date with a man and he treated me like a girl and was physically attracted to me. That is when I truly feel feminine and like a girl.

      • #760403

        Congratulations Courtney! That must have such an affirmation of your feminity!

        For me, it was the first time I fully dressed in my sister’s clothes back when I was in high school…makeup, dress, stockings, heels, wig, everything. I looked in the mirror and just loved what I saw. Unfortunately, it led to a lot of dysphoria due to the environment I grew up in and the fact that these sessions were way too infrequent.

    • #760802

      It was Halloween. I was 10 years old, without a costume. My mother worked for a girls clothing company, so she fully dressed me up as a girl! I wore a cute blouse with puffed sleeves, a red pleated skirt, bobby socks & saddle shoes. I adored everything, as I spent the entire day in school. While walking home, a nice man took my hand, and escorted me across a busy boulevard, while calling me “honey” and “sweetheart”. I loved the attention! Oh, I forgot to mention that in the morning, when my mother finished dressing me; she took me to my fathers room to show him his new daughter. I thought he would have a heart attack, as he thought I looked exactly like his deceased sister! This day made such a strong impression on me, that I’ve been crossdressing ever since. My current age is 91. Hugs, Jessie Brown.

      • #761086
        Connie Wittnee
        Baroness - Annual

        What a story!! Your memory served (serves) you well. Thanks so much Jessie for your recollection!🌹

        • #761138

          Thank you. My memory is holding up better than my looks! Jessie.

      • #761127

        What a lovely story Jessie sounds like a very cute outfit.

        • #761137

          Thank you. It was very cute, & I’ll never forget it.

    • #760812

      That did it for You! Seems like a familiar story for many of us who started that age . I was 12 and wore a girdle and stocking underdressed to school in 6th grade . The bug permanently bit and haven’t stopped since at age 76, been going out passable in public for 44 years🫦💄

    • #760813

      That did it for You! Seems like a familiar story for many of us who started that age . I was 12 and wore a girdle and stocking underdressed to school in 6th grade . The bug permanently bit and haven’t stopped since at age 76, been going out passable in public for 44 years🫦💄

    • #761007
      Emily Shy
      Lady

      I don’t really know the main defining moment it’s something I have always done ashamedly in secret thinking there was something wrong with me  it wasn’t until 10 years into my second marriage that I realised she is not going to wear stockings, heels etc as normal attire and very rare reluctantly in private settings that I decided well if you not going to wear them I will lol.

      so I’ve ran with it and loving it (she hates me wearing as well) guess a guy can’t win

    • #761033
      Laurel
      Lady

      It was the very first time I slipped into a pair of Hanes ultrasheer, jet black, control top pantyhose with reinforced toes. Carefully gathering them up. Pulling them over my foot. Sliding them slowly, carefully, sensuously up over my calf, knees, thighs and then the exquisite moment they slid over my bottom and nether regions. Rubbing my legs together and sliding my hands up and down my legs brought me to climax without even touching anything else. Now in my 50’s it still feels as erotic as the first time.

      • #761071
        Rosiebeth
        Lady

        Oh I get that entirely.   First time I climax wearing pantyhose I just had my legs crossed moving my leg back and forth feeling the hose again my skin.  And all of a sudden…… uh oh.  TeeHee.

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