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Well I started around the ripe old age of 9 and stopped for while. Then around 18 my girlfriend reopened that Pandora Box of crossdressing(As you can tell, it never went back into the box) and in 1999 is the year I became open and public about my crossdressing, I have no regrets about it and just got a few black eyes for it. But I lived though it. Duh, if not I would not be telling my story. Hehe
I went from just wearing a few things, to having a flown blown wardrobe. (That just so happens to be enough for 20 women. Yeah, The Pink Fog kidnapped me for a while there, but hey, I got some great vintage stuff from the 1800s out of that Pink Fog stage)
I went from mainly man, to super girly trying to pass(see footnote) and now in my current stage, I have settled down to hairy ass gender bender. Now I feel like I found the real me. I can be my natural manly self, with a touch of girly. I guess just like a real living breathing cis-female tomboy would be.
Well that’s my 3 main majority of stages, sure there has been a few small ones, but these three stages that had the most influence on me.
Hippie
Footnote;
Do you remember when I said I didn’t care about passing, well I lied and this stage didn’t last long though. It just wasn’t me and I wasn’t happy with myself back then either. It’s a time in my life that’s hard for me to talk about and sometimes I tried to forget about that part of my life and past. But I can’t hid or forget about it. Its part of what that makes me, ME
That’s so open hippie thank you for sharing I have just gone turbo in to girl mode from not thinking about anything girly to transitioning almost over night (taking me forever to write this as I’ve just put my nails on) ha x your posts are always inspirational xx
OMG! You really think i’m inspirational. No one never said I was inspirational before.
You have me smiling from ear to ear.
Hippie
Mine was trying panties, and never wearing boy undies from that point, and then trying the whole girl thing, got a crap wig, makeover, went out in a bigger city to support groups and friendly bars, but never really felt right…then once I met my GF she is very open to me wearing whatever, so I’ve settled into a “blurring the lines” area, where I wear pretty much all female things every day, but they “could” go either way, so womens jeans and shoes like tennies or booties with no noticeable heel, womens hoodies and tops but again, could go either way but are probably more female, womens glasses, and my hair is a sassy shorter, highlighted way that is more girl, always have my toes out and pretty colors in the summer with strappy sandals, toe rings, anklets, etc. and I love bras, so wear one whenever I can conceal it under cooler wearther clothing…So i get my fix by being a boy that really likes girl things..I dont do the whole passing thing, dont go out in public in a skirt and heels as its too small of community here, and I dont have any problems with anyone. Perhaps a few strange looks when I’m wearing black leggings and an animal print hoodie out and about, but i’m in pretty good shape , carry myself more female when trotting around, and dont care what others think!
Another thoughtful post, Hippie.
I guess in my much younger days my dressing was mostly erotic, it would get me excited. Then in my somewhat older days the desire to go out and ‘pass’ but fell far short, such w2as life for me in the early 1980’s. over the next almost 40 years there was the occasional dress event covered up quickly (with the fear of being found out). Fast forward to 2019 when the desire to dress came out of nowhere and the desire to wear women’s clothing was overwelming. Now I am underdressed every day and fully dressed when at home. Sometimes the work it takes to shave and present as feminine is to much work and at other times I go all the way, out shopping with a dress or other feminine clothes. I love being myself (Cassie).., .. Cassie
I am not sure when I started, I am sure it was when I was in single digits as to my age. Like most it was with my mother’s clothes. I can recall the first piece was her slip the feel was magic. Slowly I progressed. I also recall very vivid trying her lipstick on in the bathroom for the first time. I can still recall the smell and feel of the lipstick it was truly transformational for me. Like others it was mostly erotic at the time.
Over the years I tried stuff on her stuff whenever I could, (always wonder if she knew). Later in my late teens, I recall seeing a magazine with a Pre-Op trans in it and was fascinated by it. It was a nice feeling knowing that I wasn’t the only one who liked dressing and wanted to be a girl.
I married my HS sweetheart 40 yrs ago. In time while dating and one night at the drive in, I told her I have tried on female clothing and liked it. I don’t recall why it came up, but I am sure we both had a lot to drink and were fooling around in the back seat at the drive in. Never really discussed it after that till after we were married, and we started experimenting with me wearing panties and nylons on occasion. Life moved on, kids and work and the dressing took a back seat for many years. Although every now and then I would slip on a bra for a little while or try on some of her clothes, but only to put them on and take them right off. This continued on and off for many years.
About 15 years ago the urge hit me hard and hasn’t left. I asked my wife if she would mine is I wore panties and thi highs on occasion, she was fine with it. Needless to say that wasnt enough and kept going a little further each time. It progressed to clothes and make up, nail polish, Wigs, shaving my body and wanting breasts. My wife has always loved playing with my nipples, and I always had some breast tissue since I was young, I started pumping them and they did get a little bigger, she liked that as much as I did. 4 or 5 years ago I ordered Estrogen online and started taking them. I did see some breast growth but was nervous about taking it without a Dr supervision. I looked online and found a Dr who works with Man wanting to transition online, worked with her and went on full HRT, stuck with it for year, my blood levels finally said i was female, was a great feeling. I loved it and I felt wonderful. My goal was never to fully transition as family, work and life, just wouldn’t work for me. But it gave what i wanted most Breasts, i am now a full B cup/small C with nice shape. Body hair diminished to almost none and skin was so much better. (I never told my wife I was taking hormones) and that bothered me. The drawbacks to being on hormones was the total loss of sex drive and that bothered me, so I stopped the HRT after about 13 months. Although I have started again for a few months and then stopped a few times since and have thought strongly about going back on again.
My wife is still very supportive with my dressing and i travel often on business, so I get the chance to dress often. At home it is underdressing as one of our daughters still live with us. My wife’s only real limit is she does not want to see me fully dressed (with make-up wig). I wish she would, but she says she isn’t ready. Funny she doesn’t mind seeing my pictures with me all done up and will give me tips and buy clothes and make up.
So that is my timeline and were I am today.
First, the infant, about 4 years old, loving the swimming costumes, skirts and dresses, the gentle, happy female ways and wanting to share in them.
Next the young boy, still loving the clothes for girls, and the gentle, feminine ways, beginning to hate the more boisterous boys, and wishing he wasn’t one, feeling trapped. Being punished for dressing up from his sister’s dressing up box.
Then the teenager, taunted by the very sight of the lovely girls, who by now we’re beginning to avoid him in favour of the more sporty, “hard” boys. No soft artist/musician for them. Taunted further by the frustrated games teacher, with his threats of frilly knickers and short skirts, and games of hockey with the girls. Other incidents all adding up to the realisation that the teenager is a cross dresser, to add to the already burgeoning list of things to be bullied for, and the teenager tries to end his life right there, because, no matter how bad it currently is, it’s going to get worse, big time.
Next the rock musician, living faithfully to the rock and roll dream. No money, no home, just a band and a guitar. No opportunity for dressing, but the thoughts are always there, no matter how far back you push them.
Then the student, keeping the secret, fixing a lock to his study so his housemates don’t see him in his chosen study attire. The single respite a girl of similar size, who dresses him in her clothes for a fancy dress party.
Next, the worker, climbing the tech ladder, with girlfriends who leave him on discovery of his little secret.
Then the husband, married to the one who hasn’t found out yet due to his expertise in hiding. The growing bags of clothes held in secret in the attic, where she will not go. The constant forays out of the house into the garden to taste the air en femme. The occasional fancy dress parties where makeup is applied inexpertly.
After this, the woodland walks, and the coming out, due to the realisation that this isn’t going away, but there’s a greater need, even than the marriage – but not greater than the family or their security.
Following the coming out, the trips to the shops, and to other towns, the trips getting more and more adventurous until they become the “ordinary” femme experiences. Living tastes of life en femme, and feeling the epiphany, the revelation that life can be greater than the sum of its parts, feeling the liberation flowing through life, the realisation that the only thing to be afraid of is fear itself, and that anything is possible if you apply yourself to it – but first:
Know yourself. Your self and the limitations you see. Take baby steps. Break boundaries one by one, protecting what needs to be protected.
It’s not a race, it’s a journey which may require several changes, and pauses at interchanges.
And may 2022 be the very best part of your journey so far!!
Love Laura
I believe that I did the same little boy tuff we all did, and got the “boys don’t DO that!” talking to.
When I was 23, I had long hair, was living with my wife to be. She went out of town to visit her folks. She had this dress that she called her “rubber dress”. It looked like black normal fabric, but was REALLY stretchy and felt like rubber. While she was away, I decided to brush out my hair, stretch it over my frame and stuff the chest are to create boobs. I saw a blocky hideous thing that told me it was a mistake. I put that whole thing out of my mind…
When I was 42 I had a friend that liked to dress and BEGGED me to let them dress me up. The pic is in my public photos titled “Awkward”, I still wasn’t liking what I saw, but after that evening, I had a problem. I wasn’t able to put it away again… for some reason I felt a little prettier, a little more like, “this could be something”.
In Feb 2020(before lockdown) I happened to come out to my Mrs as a CD. It wasn’t my choice of time. I had met someone on another chat forum that seemed to have similar dressing interests and we traded pics. No big deal. Well, they did a reverse image search and threatened to tell my wife and family if I didn’t pay up…well, I decided that… I made the bed, I have to sleep in it. I told my wife. First she said, “it’s ok, screw this person. If the family doesn’t like it screw them…wear what you like.” She got a bit protective. Then came the trust concerns since I kept it from her, we had to have a lot of long talks. Finally came the “well, I’m kinda glad…I am glad there’s more that the ‘macho guy’ exterior that I’ve seen for the last 20 years”.
From there, it grew into to going out together to small things, then going to DCCR in Palm Springs last April….then DLV for Halloween this year.
I still like the full femme times, but I’m enjoying a more androgynous exploration also lately. I’ll post some pics soon…but one example already up is “went to PRIDE” pic I posted. I’m wearing whatever clothes I want, with/without makeup, and with/without a wig…
I went to the symphony with my wife in a Christmas sweater, jeggings, cute little ankle boots, light eye makeup, and my purse…FUN!
So, that’s my CD progression in a nutshell…
Have fun out there!
XOXO
Rayna
I started when I was around 9 or 10 by wearing some of my mother’s clothes, I thought that she looked good in them so I thought that they would do the same thing for me. She would catch me and tell me that boys don’t wear girl’s things but after a few times we talked about it, and she finally relented and just said not to wear any of her new clothes. When I was 14, she helped me dress in an old poodle skirt, sweater, bobby socks and saddle shoes and even got a wig for me along with a training bra and sent me out to take my younger brothers and sister. She had even done my makeup to the point that I was semi passable to the point that people referred to me as a girl. I stopped dressing when I got too big to fit into her clothes and while I was in the military. I started again after I got out and met a girl that I talked about it, and she was all for it for a short time then things changed and so I stopped again. When I met my first wife I just didn’t think about again and after we got divorced, I had another girlfriend who came up with the idea of me dressing for her and it brought it back into my life. Well, I finally met the person that would become my second wife and almost as soon as we started dating, I told he about all of it and that I was Bi (discovered after the military while out drinking and meeting someone and going back to their place), she said that she was ok with it because that was what made me who I was. I still kept it a secret from all but a few friends that we met through an adult site that she had gotten us into, and they met Danni at a costume party for Halloween. I have been dressing every once and awhile ever since and have since let my oldest daughter, one of my sisters and one of my brothers and his wife know about my dressing. I am now 70 and the love of my life has passed (she passed a little over a year ago) and I don’t care what anyone thinks because that is who I am, and I enjoy the feeling of dressing up, putting on my makeup and wearing panties, bra, hose and high heels. I may not be passable, but that’s not what matters to me, what matters is how I feel.
3 to 6 years my sisters and their friends dressed me in their clothes and took me to the local park as their sister. Started school and it went away.
Come to 12 years and found some underwear and petticoats my sisters were disposing of so took them and tried them on. Loved the feeling so hid them away and only used them, along with additional sisters’ clothing, when able. Left home at 16 so it went away again.
Married, had children and raised the family. Around 30 years got the urge again so purchased some nice underwear, bras and panties half slips and used my wife’s dresses, skirts and tops. Went for about 5 years changed jobs and dressing ceased. I stored the clothing for later.
Now retired and home with wife and self so Requal returned. Pulled out the stored clothing and purchased some new nice underwear along with skirts and tops and Requal appeared two to three times a week.
Unfortunately the family dynamics changed so Requal has once again been sidelined to when able; being 2 to 3 times a month, if lucky.
Started at 13 with my mom’s lingerie/nighties and I’ve been hooked on lingerie ever since. First lingerie shopping trip was at 16 and by the time I was 20 I had a lingerie wardrobe most girls would be insanely jealous of. During this time I was also starting to become more and more interested in guys, and by 20 I had my first (and still current) boyfriend who has had a huge supportive and encouraging role in my journey.
Hi I started around the same age as you.started with sister clothes and shoes I loved it never had to really take a break from it I kept it secret and I use to dress in patties 5 or 6 times a week while keeping male outside but inside I new I was feeling sexy around 2003 I went to a c/d gay bar I chatted with sandy she gave me the name Jennifer in 2 weeks I was back dressed and nervous as all hell I love it damm COVID haven’t been able to go out to the bar
Peace and love Jennifer Sullivan
ALike most everyone else that has given their time line, mine started when I was about 12 years old or maybe even sooner. My younger sister had three petticoats that I really liked. One was pink, one was white and my favorite was a sky blue one. One day I was home alone and went into her room and found the three petticoats in her closet. I took them into the bathroom and put them on in layers so they looked like I was wearing a gown When I looked at myself in the mirror I was hooked. Every chance I got to wear her clothes, I did until one day she came home unexpectedly and caught me. She was shocked when she saw me and told that if I wanted to wear girls clothes to buy my own and leave hers alone. That stopped me for awhile until I was out of school living on my own. I began buying lingerie and women’s clothes until I had quite a collection of feminine things that I’d wear in the privacy of my apartment. It was years later before I started going out dressed en femme to various places like restaurants and malls and still do but not as much as I used to mostly because of the pandemic keeps me from socializing.I did go on vacation three years ago and lived as a girl for the entire time I was on vacation. That had been a fantasy of mine for a long time and I finally got to do it. I don’t know what tomorrow’s going to be like, but I don’t think that I’ll ever stop crossdressing. I still get fulfilled and enjoyment by getting dressed en femme
I had a fairly unpleasant start – I was 14 and bullied at school for, among other things, being a bit overweight. Eventually the joking about me needing a girdle (this was the late seventies) resulted one day in me being physically forced to put on a girdle. And, once they had photos, I was given the choice of making it a permanent addition to my uniform or see the photos distributed far and wide. So, with great difficulty as you might imagine, I had to adapt to life wearing a firm long leg panty girdle daily under my uniform. They did check on me daily, so I couldn’t cheat. As I was excused gym class on medical grounds, I didn’t even get the occasional day off.
When I left school, I’d got used to being in a girdle after all that time, but I didn’t want to continue. But I had panic attacks when I tried to stop – I guess a subconscious fear of being caught – so I reluctantly went back to it.
I don’t fully crossdress – I tried once, but it did nothing for me and I’d never pass in a hundred years anyway – but I wear a girdle and bra every day.
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