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Registered On: October 3, 2019Topics: 12Replies: 155Has thanked: 532 timesBeen thanked: 1113 timesFor 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.
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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.
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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.
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.
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Registered On: June 26, 2019Topics: 24Replies: 468Has thanked: 1757 timesBeen thanked: 2353 timesThis 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.
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- Registered On: September 13, 2019Topics: 5Replies: 491Has thanked: 0 timesBeen thanked: 1873 times
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.
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- Registered On: December 17, 2022Topics: 4Replies: 27Has thanked: 146 timesBeen thanked: 191 times
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
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- Registered On: September 20, 2021Topics: 2Replies: 66Has thanked: 18 timesBeen thanked: 333 times
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.
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Its strange how “the fever” justs grabs us isnt it?
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- Registered On: September 13, 2019Topics: 5Replies: 491Has thanked: 0 timesBeen thanked: 1873 times
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.
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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!
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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
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When I go up in heels, magic happens
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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
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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
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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
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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.
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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
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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.
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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.12 users thanked author for this post.
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.
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- Registered On: April 7, 2021Topics: 1Replies: 622Has thanked: 2312 timesBeen thanked: 2811 times
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.
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me too!!!
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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.
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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
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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.
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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.
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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
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Edie, Your response here echoes my experience to a “T”. Well written and so right on for me too. 😉😊
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- Registered On: October 9, 2018Topics: 1Replies: 200Has thanked: 1228 timesBeen thanked: 691 times
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!
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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
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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.
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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!
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- Registered On: April 25, 2019Topics: 18Replies: 181Has thanked: 396 timesBeen thanked: 1036 times
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.
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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.
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- Registered On: May 11, 2020Topics: 12Replies: 924Has thanked: 1002 timesBeen thanked: 4227 times
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.
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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.
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- Registered On: August 15, 2020Topics: 42Replies: 651Has thanked: 2293 timesBeen thanked: 3284 times
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.
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- Registered On: May 26, 2021Topics: 12Replies: 390Has thanked: 2393 timesBeen thanked: 1741 times
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.
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- Registered On: October 13, 2022Topics: 14Replies: 49Has thanked: 75 timesBeen thanked: 293 times
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!
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- Registered On: November 27, 2017Topics: 3Replies: 67Has thanked: 153 timesBeen thanked: 209 times
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.
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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.
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- Registered On: November 1, 2021Topics: 24Replies: 638Has thanked: 10484 timesBeen thanked: 3605 times
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
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- Registered On: November 23, 2019Topics: 1Replies: 432Has thanked: 272 timesBeen thanked: 1824 times
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.
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- Registered On: August 8, 2022Topics: 11Replies: 151Has thanked: 163 timesBeen thanked: 695 times
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
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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
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That’s Sherri with one s not two, gees, I can’t sing my own name.
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- Registered On: December 2, 2021Topics: 4Replies: 484Has thanked: 3127 timesBeen thanked: 2084 times
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
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- Registered On: June 14, 2021Topics: 31Replies: 1794Has thanked: 12842 timesBeen thanked: 8997 times
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.
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- Registered On: March 16, 2022Topics: 1Replies: 342Has thanked: 1503 timesBeen thanked: 1319 times
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
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- Registered On: February 27, 2020Topics: 2Replies: 1069Has thanked: 5404 timesBeen thanked: 4709 times
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.
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- Registered On: January 9, 2021Topics: 20Replies: 265Has thanked: 783 timesBeen thanked: 1636 times
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.16 users thanked author for this post.
- Registered On: November 18, 2019Topics: 1Replies: 285Has thanked: 261 timesBeen thanked: 1058 times
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.
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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.
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I love this, what a brave moment.
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- Registered On: January 21, 2021Topics: 1Replies: 77Has thanked: 498 timesBeen thanked: 384 times
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.
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- Registered On: April 13, 2020Topics: 27Replies: 217Has thanked: 952 timesBeen thanked: 1402 times
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
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- Registered On: November 27, 2022Topics: 6Replies: 89Has thanked: 227 timesBeen thanked: 527 times
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.
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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.
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- Registered On: January 8, 2020Topics: 5Replies: 420Has thanked: 1827 timesBeen thanked: 1798 times
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
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- Registered On: July 20, 2020Topics: 7Replies: 498Has thanked: 6807 timesBeen thanked: 2453 times
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.
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- Registered On: November 16, 2022Topics: 1Replies: 30Has thanked: 208 timesBeen thanked: 212 times
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
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- Registered On: September 11, 2021Topics: 0Replies: 33Has thanked: 30 timesBeen thanked: 172 times
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!
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- Registered On: November 5, 2019Topics: 14Replies: 675Has thanked: 2591 timesBeen thanked: 3288 times
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
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So jealous, that must’ve been awesome to have a mom give loving help.
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- Registered On: August 23, 2015Topics: 3Replies: 270Has thanked: 7829 timesBeen thanked: 1170 times
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.
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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.
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- Registered On: October 15, 2019Topics: 63Replies: 288Has thanked: 931 timesBeen thanked: 1652 times
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!
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- Registered On: October 27, 2022Topics: 5Replies: 170Has thanked: 347 timesBeen thanked: 756 times
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.
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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.
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- Registered On: November 20, 2022Topics: 2Replies: 108Has thanked: 120 timesBeen thanked: 444 times
There have been many significant moments in my journey as a crossdresser, but I can’t think of a single defining moment. My journey has been one of slow, steady progress.
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- Registered On: August 1, 2020Topics: 9Replies: 1406Has thanked: 5124 timesBeen thanked: 6445 times
About five years old putting on my sisters dress, that did it for me.
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- Registered On: October 3, 2019Topics: 12Replies: 155Has thanked: 532 timesBeen thanked: 1113 times
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.
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