- September 27, 2023 at 1:12 pm #769044Patti MyselfParticipantRegistered On: September 25, 2023Topics: 5Replies: 68Has thanked: 166 timesBeen thanked: 333 times
To me it was when I finally realized what I was…finally found a word that fit, but the strange way I found it. And that word was ‘transvestite’. And finding it after so many years that I had been doing this weird thing of wanting to wear girls clothes as a young, and very naive boy.
This was long ago when the only guys I saw dressing up as females were comedians on TV who were just doing it for laughs. I had no idea that there was anyone else like me. I must have been some kind of freak to do this…probably the only one in the whole world. But I couldn’t stop. It was too tempting and those feeling were with me always. Sneaking around whenever I could trying on my mom’s things. Knowing I needed even more. This went on for many years as I grew up. Liking girls in grade, junior high and high school but also wondering what it would be like to wear their clothes. Looking at them and dreaming of wearing their dresses, shoes, nylons and whatever they had on underneath.
I was in my first year of college and my roommates always had Playboy magazines laying around. I was leafing through one of them one day and came to a photo spread of something called ‘fetishes’. A new word for me. As I looked at the various graphic (at least for those days) photos I saw one where there was a guy stretched out on a table wearing a bra, panties, garter belt, nylons and high heels. My mouth fell open. There was also a dominatrix type of lady standing next to him holding a whip. The caption below the photo said something like “Example of transvestite sadomasochism.” Even at my age of 18 I’d never seen those two words. I soon went to the library looking up those words and there was very little information about either. But I did find one book referring to transvestite and that was a work about an old character who may have been the first….The Chevalier d’Eon.
So there I was, a late teenager who had been a transvestite almost my whole life without knowing there was a name for it or that I wasn’t alone. But I still had a long way to go to figure it all out. The rest, as they say, is history. But I’m still amazed that it took me that long to finally begin to understand that what I was doing was, in an off-beat way, normal. I have to feel sort of stupid for being that naive even way back then. But I also remember exactly that moment when I first saw that photo, and what a game-changer it was for me.
How about you. Did you have an Aha moment with your crossdressing that made you more aware?
Total of 27 users thanked author for this post. Here are last 20 listed.
- October 8, 2023 at 10:29 am #771187BrandiCD11LadyRegistered On: October 7, 2023Topics: 11Replies: 188Has thanked: 281 timesBeen thanked: 372 times
I was in 5th grade and I had an operation on my ear (that is how I know). Was home alone and found my way to my parents room and located in my mommy’s dresser found an all in one bra. It was so soft tried it on and as they say the rest is history.
- October 3, 2023 at 2:10 am #770098Barbara ZellLadyRegistered On: July 4, 2020Topics: 1Replies: 7Has thanked: 7 timesBeen thanked: 26 times
I had that moment too when I admitted to myself that I was a transvestite. The classification felt right and since I had started to go out as Barbara it was a realization that helped me along the way. I was able to look into transformation services and order items that made me more feminine that I had avoided previously.
Once I had accepted myself and classified it I no longer was afraid of presenting myself out to the world but still cautious of what the world thought.
- September 30, 2023 at 7:03 am #769522Staci GalLadyRegistered On: August 9, 2022Topics: 2Replies: 108Has thanked: 71 timesBeen thanked: 537 times
All my life I would see gals wearing cute clothes and thinking how nice the clothing looks. My wife would wear a cute sundress or skirt and I would think how cute and comfy she looked in her clothing. About six years ago, I told myself, I can do that too!!
That is when the “Ahhh” moment struck. Why should girls have all the fun?
I found a cute LBD, tried it on and was hooked. Glad I did it, don’t regret one moment, just wish I had done it sooner.
Crossdressing for me in a very enjoyable and relaxing activity that is also fun. Staci.
- This reply was modified 2 months ago by Staci Gal. Reason: typo
- September 30, 2023 at 7:12 am #769525
- September 30, 2023 at 3:05 am #769486Alison AndersonDuchessRegistered On: October 15, 2018Topics: 18Replies: 1247Has thanked: 981 timesBeen thanked: 5271 times
I probably had two Aha moments.
During my early years and teenage years, dressing was a fetish for me. But one time after I got married (in my early 20’s), after peaking, I kept the skirt on. I discovered that the skirt was quite comfortable to wear even without being sexually stimulating. Not that I didn’t enjoy the fetish aspects, but that I could wear it without being a fetish activity too.
At age 52, due to a breakdown in my marriage, and having seen enough crossdressers on the web out in public, I went to a nearby transformation studio for a makeover and a trip out to eat at the diner. Within 6 months I was attending parties at this woman’s home where I met many other crossdressers and supporters. This went on for 9-10 years before things changed in her life and she eventually had to move away. But this gave me the experience of doing my own makeup and going out in public with others in the group, as well as going out on my own.
- September 28, 2023 at 11:32 pm #769319Fredrika JonesLadyRegistered On: February 24, 2021Topics: 1Replies: 533Has thanked: 629 timesBeen thanked: 1894 times
It just hit me one day. I was in a thrift shop heading for the men’s polo shirts. I was walking past the dresses when something made me stop and look. My eyes fell on a particular dress and I just reached out for it, grabbed it off the rack, and took it to the dressing room. It fit just fine, so I bought it and took it home. That’s how it started with me. Both the male and female parts were pleased, and I just keep growing into it.
Hugs and Kisses,
- September 28, 2023 at 7:46 am #769195Marg ProdueLadyRegistered On: March 16, 2022Topics: 2Replies: 583Has thanked: 3065 timesBeen thanked: 2327 times
As I’ve mentioned before. The moment that I went to renew my Student Pilot 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. I didn’t and wasn’t crossdressing then. People actually saw me as a woman and I thought 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 Patti for this interesting question. Marg Produe
- September 28, 2023 at 7:31 pm #769293DaniLadyRegistered On: March 22, 2022Topics: 6Replies: 86Has thanked: 895 timesBeen thanked: 460 times
About five years ago. I found a whole bunch of people just like me. The guilt, shame, embarrassment could leave no. I wasn’t a freak. It was definitely an ah-ha moment alright. I just think of all the time that went by. And all the self doubt and guilt. At least it’s better now.
- September 28, 2023 at 7:58 am #769200Patti MyselfLadyRegistered On: September 25, 2023Topics: 5Replies: 68Has thanked: 166 timesBeen thanked: 333 times
Thank you. I’m really glad I started this thread. Have been so many great ‘Aha’ moments shared. Hopefully there will be more. Yours is really unique that it happened when you were in male mode not trying to present femme. Yet it was perfect timing for you to awaken the real you and now look. So happy for you. And thx again for sharing! :)
- September 28, 2023 at 7:27 am #769187Julie DayDuchessRegistered On: December 20, 2022Topics: 1Replies: 173Has thanked: 162 timesBeen thanked: 731 times
My “aha” moment was when I tried on the first dress I had bought in 2019. I loved the way it felt, and I had just discovered this site and notices how beautiful the girl were. That when I went out and bought my first dress, as I started to buy more feminine things and tried on makeup, I know this is what a always desired to do. Then when I had my first makeover, I have evolved my look and found who I REALLY AM.
I am now very comfortable with my feminine look and knowing I share this trait with so many wonderful girls is comforting and so wonderful. I love presenting as Julie I only wish I could express this side of me more frequently.
I agree with Chrissie, I feel I am making up for lost time. I have always had these feminine feeling but was to afraid to act on it. I am so glad I did, it is worth all the difficulties I have had. My wife still dies not accept this side of who I am, and this is who I am and nothing can change that.
Thanks you the post Pattie, you are such a lovely women.
- September 28, 2023 at 7:35 am #769189Patti MyselfLadyRegistered On: September 25, 2023Topics: 5Replies: 68Has thanked: 166 timesBeen thanked: 333 times
Wow Julie…thx for saying what you did about me being lovely. I am more now that I was many years ago. But it took time and a lot of struggles. And I don’t mean about my looks…I mean about my personality. And I think that’s what you mean too. And it’s why I came on here a few days ago. I have so many things I can share in a positive way after all I’ve been through. Most of my struggles were my own fault and I now recognize that. But I also realize that we all have to move forward and not focus so much on our past. Just learn from it. I’m at an all-time high in my life and love shouting about it! THX SO much! xo :)
- September 28, 2023 at 8:05 am #769202Julie DayDuchessRegistered On: December 20, 2022Topics: 1Replies: 173Has thanked: 162 timesBeen thanked: 731 times
Pattie, we all grow in life, it the people that realize that makes it so important in who we are. When you can accept your self with all the faults and mistakes in like that make you a wonderful person. Yes I DO MEAN about your personality. I am so glad you did find CDH and meeting you as been such a pleasure, I love your insight. Yes, you also look gorgeous as well. I look forward to chatting with you.
- September 28, 2023 at 7:01 am #769178StephaniewyLadyRegistered On: September 24, 2021Topics: 27Replies: 342Has thanked: 2303 timesBeen thanked: 2022 times
Always secretly played around a bit with moms things, then girlfriends and then wifes but kept all very repressed while growing up, but knew deep down that there was something else. At 62 slipped on my wife’s bra and Aha I knew it was time to admit and let stephanie come out. Wife was totally supportive and wished I would have dealt with it earlier..I wish I would admitted it long ago.
- September 28, 2023 at 5:33 am #769144JOJOBaronessRegistered On: August 5, 2018Topics: 0Replies: 152Has thanked: 631 timesBeen thanked: 788 times
- September 28, 2023 at 5:29 am #769143Ria FreichukLadyRegistered On: June 6, 2020Topics: 2Replies: 193Has thanked: 845 timesBeen thanked: 856 times
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- September 28, 2023 at 4:56 am #769141Kim DahlenbergenLadyRegistered On: November 18, 2019Topics: 1Replies: 499Has thanked: 603 timesBeen thanked: 1979 times
I had to think about this a bit to identify a moment when things changed for me. For me, it seems I gradually evolved, with few stark moments of realization. But one moment does stand out.
I had been underdressing for years with the full knowledge and tolerance of my (then) wife, but she was less than enthusiastic about me dressing completely as a woman, and honestly, I had my doubts about how I might loo.
It happened that she accepted a job that involved weekly travel, which left me on my own several nights a week. I filled much of the alone time trying on a few of her tops and skirts, those most able to accommodate my somewhat larger physique. Then one night I tried her makeup for the first time. The color match wasn’t perfect, but it was OK and after a bit of practice, I got to the point where I could look at myself in the mirror.
My aha moment came when I had finished a practice session with makeup, gotten dressed in a top and skirt, and checked out the results in a full length mirror. I saw a woman. In that moment, I saw myself in a different way. Instantly, I thought, “I CAN do this!”
Doubts erased, I started dressing fully, regularly at home. I began to acquire my own clothing and a very rudimentary makeup kit. Within weeks, I had ventured out for the first time, gotten a wig and a makeover. Soon thereafter, I was living my day to day life totally en femme and honestly, loving every moment of my newfound freedom.
- September 28, 2023 at 4:34 am #769137
- September 28, 2023 at 3:36 am #769132Kay JacksonLadyRegistered On: August 26, 2023Topics: 5Replies: 60Has thanked: 65 timesBeen thanked: 311 times
Not dissimilar to your story.
I had a limited amount of femme clothing and a lot of borrowing from family, didn’t understand, thought I was the only one in the world but generally enjoyed myself.
When I started my paper round aged 13, I used to read quite a few of the more sensational papers that we didn’t get at home. Amongst them one featured an article about Romy Haig looking gorgeous on a date with David Bowie. Within the article the word transvestite appeared.
A bit of research later (no Internet then of course so every dictionary and encyclopedia I could get my hands on) and I knew what I am. Not why, just what I am.
- September 28, 2023 at 6:29 am #769164LadyRegistered On: September 25, 2023Topics: 5Replies: 68Has thanked: 166 timesBeen thanked: 333 times
THX for your Aha moment. Very similar to mine where we both thought we were the only ones. But were able to find out later that we weren’t. I’ve always found it interesting that way back then the term was transvestite when crossdressing was not yet coined. Now transvestite has all but disappeared…probably a good thing. Aha! :)
- September 28, 2023 at 2:13 am #769131Annabel BrookeLadyRegistered On: March 19, 2021Topics: 1Replies: 25Has thanked: 3 timesBeen thanked: 156 times
Aha!, that was when id acquired my own set of clothes, make up, wigs and had some longer periods to dress. That was when i really started to enjoy the dressing and thought being a transvestite isn`t such as bad thing.
- September 28, 2023 at 2:03 am #769130Suzanne MartinHostessRegistered On: January 8, 2020Topics: 9Replies: 806Has thanked: 7572 timesBeen thanked: 3412 times
Enjoyed reading everyone’s stories. It is nice to hear that I’m not the only one that felt they were alone growing up. Like others have said I wore my mother’s panties and bras as well as slips, stockings, garter belts and dresses. Always when hone alone and for brief periods of time so I didn’t get caught. My mother was an Avon rep so we had samples, particularly lipstick, in the house all the time. My sisters and I would play with them at times. I had 3 sisters (no brothers) and we played house and Barbies all the time in the winter, also colorforms and paper dolls. Throughout my life I had periods where I would wear some type of lingerie for brief periods. One year while in college I did dress fully for Halloween. It was a real rush for me. A couple years ago I came out to my wife and have been dressing since. I think when I came out to her was my aha moment. Since then I have increased the amount of time I spend dressed, am able to dress when my wife is present, learned to use make up (it’s a work in progress) and amassed quite a wardrobe. I don’t go out in public but hope to at some point, although I have underdressed a few times.
Thank you to everyone that has shared their story.
- September 28, 2023 at 6:34 am #769166LadyRegistered On: September 25, 2023Topics: 5Replies: 68Has thanked: 166 timesBeen thanked: 333 times
THX so much for your wonderful Aha story! You were lucky to have sisters. All I had was one brother so I didn’t have any of the opportunities that you did with family even though you were still pretty much closeted and wondering. So happy for you that your life now can include your femininity with your wife fully involved. Being alone with these feelings is so sad because we all need support and understanding. Luckily I have it now too. Thanks so much! :)
- September 28, 2023 at 1:58 am #769128Roberta BroussardDuchess - AnnualRegistered On: July 20, 2020Topics: 7Replies: 687Has thanked: 8796 timesBeen thanked: 3535 times
About 3 yrs ago I started fully dressing. About the 3rd or 4th time, I took a good look in the mirror and saw Roberta, a woman looking back at me.
It’s then that I realized that I had finally found me.
- September 27, 2023 at 10:54 pm #769112Tiffany GreeneLadyRegistered On: May 19, 2021Topics: 5Replies: 65Has thanked: 114 timesBeen thanked: 471 times
I had been wearing my mom’s heels around the house for years (in secret) from 5 or so years on… but I guess the Aha Moment would have been when i was flipping through the channels after school maybe around 11 years old, one of the talk shows (maybe Rikki Lake? Not even sure if that name is correct) featured crossdressers. I was in shock that there were more like me but I couldn’t pause on the channel that long for fear of my curiousity outing me to other people that were in the room at the time. You can bet I researched it at the library and anywhere else i could find info in the days before the internet.
- September 27, 2023 at 9:57 pm #769099Heather SmithLadyRegistered On: May 15, 2023Topics: 3Replies: 102Has thanked: 30 timesBeen thanked: 474 times
I’m 78. My “Aha” moment was when I was 74. In response to me complaining about something (I’ve no recollection what), my wife said, “You just need to pit your big girl panties on and deal with it. They have some pretty ones.” My mind immediately went back to when I was in the 12 – 1t5 year old range and had on a few occasions, tried on my mom’s bras (using oranges as forms), slips and girdles. It wasn’t often as I have 2 brothers. I only did this when I was home alone. Anyway, when my wife made the comment, I immediately knew I wanted to buy some panties. That was in mid-June 2020, and I haven’t quit wearing panties since, About 3 months into wearing panties, I tossed out all my Jockey shorts. I only wear lace hipster panties now. My wife was taken aback when I told her (mid-November 2020) that I thoroughly enjoyed wearing panties. I now dress at home as often as I want. My wife has only seen me a few times with a wig, lipstick, and earrings on. However, she’s seen me twice in the past few days. While we agree no family/friends should learn I CD, I have been out dressed on maybe 10 occasions now. I took to CDing like a duck takes to water. I only wish I could CD 24/7 as I love dressing in women’s clothing. I now dress outwardly at home at least 50% of the time.
- September 28, 2023 at 8:45 am #769214JoanarbourLadyRegistered On: April 5, 2016Topics: 1Replies: 41Has thanked: 95 timesBeen thanked: 158 times
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- September 27, 2023 at 8:53 pm #769095Peggy Sue WilliamsDuchess - AnnualRegistered On: June 26, 2019Topics: 27Replies: 557Has thanked: 2133 timesBeen thanked: 2924 times
I had been crossdressing in the open since I was about five y.o. and served as a flower girl in a wedding. I was fortunate to have female mentors along the way who schooled me in the female arts. It was just so normal and so much fun to alternate between being a girl and being a boy that I never gave it much thought, much less think anything was “wrong” with it. Girls were fun to be with, and they were encouraging. There were long periods when I did not dress, such as when I served in the military.
As far as as an “Aha moment,” goes, I never gave it much thought until I was in college in the mid 1960s (no internet then). The university library did have loads of reading material about “transvestites” and gender dysphoria, along with other material which we now know is completely in error or misleading. I was left more confused then ever, if not afraid that I was some sort of nut case. I think by the 1970s when magazines like Penthouse started publishing real life information about crossdressing is when I had more of an “Aha moment.” Meaning there really are actual humans out there like me, and they are very normal too, hold jobs and pay taxes.
- September 28, 2023 at 6:46 am #769171LadyRegistered On: September 25, 2023Topics: 5Replies: 68Has thanked: 166 timesBeen thanked: 333 times
Excellent point about Penthouse magazine. You are so right that back then many of those mags did start having info, although much of it focusing on the erotic, but at least it was there. I remember there were forums or letters to the editor which had stories from crossdressers. Thank you for that insight. You were so fortunate to be able to be a little girl crossdresser out in the open. I was into trying on my mom’s things but mostly really wanted to wear the clothes of girls I knew in school but wasn’t able to. THX so much! :)
- September 28, 2023 at 3:39 am #769133Rachael WanttobeLadyRegistered On: July 21, 2021Topics: 2Replies: 127Has thanked: 588 timesBeen thanked: 431 times
- September 27, 2023 at 10:49 pm #769111Tiffany GreeneLadyRegistered On: May 19, 2021Topics: 5Replies: 65Has thanked: 114 timesBeen thanked: 471 times
- September 28, 2023 at 6:47 am #769172LadyRegistered On: September 25, 2023Topics: 5Replies: 68Has thanked: 166 timesBeen thanked: 333 times
- September 28, 2023 at 2:23 pm #769255Peggy Sue WilliamsDuchess - AnnualRegistered On: June 26, 2019Topics: 27Replies: 557Has thanked: 2133 timesBeen thanked: 2924 times
It was in the 1950s, and I am in my 70s now. Thus, it was a long time ago.
Very briefly, I was always around females, far more than males in my family. Moreover, I believe my CD desires started very early. I got into my mom’s makeup at age three or four, so I was told.
Although memories that long ago are fuzzy, it was a large wedding, and I was no stranger to being around females and girl things. In fact, I preferred female playmates and doing girl things. My mom told me my female cousins were fitted for pretty dresses for the wedding which I supposedly carefully observed. At some point, I too was fitted for female clothing. I find this not unusual, because I was already out of the closet. Relatives knew, and my mother knew. I can only assume there must have been no objection from the bride, who was also a relative. My guess? One my older cousins, who tended to be on the boisterous side, probably got the ball rolling on this. The one thing I do seem to remember clearly is girls get far more attention than boys do, with people always saying how pretty you look. Could that be one of many contributing factors that makes us enjoy crossdressing?
- September 30, 2023 at 6:36 am #769518LadyRegistered On: September 25, 2023Topics: 5Replies: 68Has thanked: 166 timesBeen thanked: 333 times
Thank you so much for that wonderful story. I’m sure many of us would have loved to be able to experience that kind of joy. THX so much. :)
1 user thanked author for this post.
- September 27, 2023 at 5:52 pm #769080Rachael WanttobeLadyRegistered On: July 21, 2021Topics: 2Replies: 127Has thanked: 588 timesBeen thanked: 431 times
I started with moms things as a young boy too. I knew it was “wrong”, but the incredible euphoric rush it gave me made me do it more and more. I’d stay home instead of going to play with my brother and friends sometimes just so I could raid the laundry and get moms things to wear. I even underdressed around her which was oddly exciting. I was fortunate to never get caught. After high school I got my first girlfriend and my inner girl went dormant for a long time. Until about 8 years ago when I found a bunch of panties wife was throwing away. I snuck them out of the trash and the first time I slid that pair of Victoria’s Secret panties on my girl came rushing back!! I’ve since recovered a couple of tops, a one piece Speedo suit, a little black dress and I stole one of her bras. I wish I could be more open but wife would freak out. I just hit a milestone birthday though and had a major mental shift- I’ve been dressing for a bit every single day and even underwore panties and a bra around her. I feel a collision course coming-we will see!!
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- September 28, 2023 at 6:49 am #769174LadyRegistered On: September 25, 2023Topics: 5Replies: 68Has thanked: 166 timesBeen thanked: 333 times
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- September 27, 2023 at 4:42 pm #769076Chrissie SmithBaronessRegistered On: March 13, 2023Topics: 22Replies: 207Has thanked: 615 timesBeen thanked: 869 times
Hi Patti. Interesting post!
Having read a lot of the girls’ stories here, my Eureka moment was later than most. I never tried my mother’s underwear on, and had a completely normal teenager existence. At that point I wouldn’t have heard of the word transvestite. But one day in my early twenties I suddenly experienced an overwhelming urge to put some lipstick on. I can remember the moment as if it were yesterday. I have absolutely no idea where the feeling came from but of course I tried it and the rest as they say is history!
Oh, I dressed sporadically for a year or two then got married and had a 35 year hiatus until June when I had a week en femme and a fab visit to a professional makeover service. Looking to make up for lost time now!
Hugs, Chrissie xx.
- September 28, 2023 at 6:51 am #769176
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