That was just like how I grew up. Sister, two stepsisters, dominant mother, and a stepfather who allowed the females to get away with what they wanted. Very female-centric.Originally Posted by Natalie5004
That was just like how I grew up. Sister, two stepsisters, dominant mother, and a stepfather who allowed the females to get away with what they wanted. Very female-centric.
I was in competitive roller skating and my mom purchased a pair of white tights for me to wear under my outfit. When she put me in them, them felt great. They did not work the way she intended, so that was that, but I remember the feeling. Then it was off to mom's panties and the rest is history.
Started about 4 or 5 playing with the neighbors my age (all girls.
One day at a friends house she and i switched underwear and panties.
Mom had pink strapless bra probably from teen years Used rolled up newspaper for volume She had a brown sparkly dress with a side zipper Remember them? It progressed to girdle and big girl bra more later
I think I was about 10 or 11 when I first dressed. It was definitely my middle school years and this would have been in the late 80s.Wasn't something that I'd ever even considered prior to it happening but it clearly flicked a switch inside me and parts of it remain crystal clear to this day.
I was a member of the scouts and there was a fundraising event involving various troops from the county (this is in the UK). There was going to be all sorts going on throughout the day but on the evening there would be a big show with each troop contributing one or two performances. Anyway, some time prior my Mum asked what our troop was doing for the evening. I said how one of the leaders had written a play and we were going to perform that. Being an all male scout troop is was a predominantly male play but there were a couple of female roles. Mum started asking me what it was about and I forget how or why I even brought it up, but I clearly mentioned how no-one wanted to play the female parts, at which point she suggested why don't I do it? It had never crossed my mind to prior to her saying it and I wasn't too keen either, not to mention that I thought people would laugh at me. But she said something along the lines of how it would be fun, reassured me that it would be okay and that she'd help sorting the costume out. The role itself was of a mother in a family and I eventually agreed, although still wasn't thrilled about it. Fast forward and I get home from school one day and there was a bag full of clothes that Mum had collected from my two cousins, who were a few years older than me and who had sorted some things out that they thought would be suitable. She went through everything and picked an outfit, which just ended up being a knee-length dress, cardigan and some very low heeled shoes (photos exist!). I can still picture myself looking at myself in the mirror that first time I put the dress on and thinking I just looked silly. A couple of days later, I got back from school and Mum said something about wanting to have another look at me in the outfit. I didn't understand why at the time as she'd literally only seen me in it a few days ago. Turned out she'd been shopping and brought a bra (which she padded), some tights, a few accessories like a necklace and bracelet, had got a wig from somewhere, and wanted to see what I looked like with everything on. The thing I remember more than anything is her having to help me put on the tights and the feeling that very first time I wore them (they were a low denier tan/flesh coloured pair). There was at least one more outfit run through at home, as Mum wanted to try putting me in makeup, and by the time of the actual performance, I'd become much more comfortable with the clothes and the whole idea of it. Plus there had been a full dress rehearsal, so while I did get a few people laughing at me then, come the night a lot had people had already seen me dressed by that point. Also, as the photos show, when everything was put together, the clothes, the accessories, the wig, the makeup, I didn't look too bad!
Oh yeah, and the other female role, no-one else wanted to do it so one of my friend?s from the troops sister ended up playing it! So if I'd been a bit more reluctant or just said "No" they'd most likely have just gotten another girl to play the part I did.
When I was 7 my sister and I stayed with my grandparents for a few days. My mom forgot to pack extra underwear for me so my grandma handed me a pair of my sisters and said put these on and you?ll be fine.
I started with my mom’s pantyhose around age 5. I remember wearing pantyhose under my jeans to kindergarten. By the time I was 8 I was raiding my mom’s clothes on a regular basis. By the time I was 11 I was dressing fully minus makeup. I haven’t looked back since.
Hell of a story. Coincidentally it matches closely some archetypal CDer fantasies. Of course, coincidences happen sometimes.
Wow, there are some truly detailed and delightful stories. I feel a little intimidated but for me, it began when I was 5 and I felt so comfy in my mom?s heels! I wanted to be a girl from since I was 4. Being Olivia is always a release of the girl I wish I had the courage to be. If I didnt already have such a blessed family life, my time as Olivia would be 24/7. But, I love my family and know if they ever get to a point of acceptance, then I have a chance to live as I could be. Until then I will take the times I get to let myself become Olivia and feel my life as how I feel inside.
When i was about 19 in the house alone putting on my mums knickers and bra, then it grew from there.
Don?t really remember anything of note in my childhood although I was nerdy and introverted and never really part of the cool kids or athletic groups nor dated much in HS. Age 20-60 I very occasionally would sneak putting on my wife?s panties or bra as kind of an erotic rush but didn?t at that time have any strong desire to present as a female. Early-mid 60s, around two years ago, I very impulsively purchased a summer dress that for some reason I thought would look cute on me (shopping at Costco of all places). That rabbit hole proved to be deep indeed!! Within 6 months went from that single dress to pretty much a full hair to heels multi-suitcase ?wardrobe? (albeit Temu level of quality - lol). I pretty much dress feminine to varying degrees during all my private time now.
In my case it literally happened over night. I had been wearing pantyhose for years but one day I just woke up and told my ex I wanted to try makeup. That opened the floodgates.
We went shopping that same afternoon. I suddenly had lingerie, a dress, skirt, heels, makeup, purse, and every other item a woman would have in her wardrobe. She even taught me how to make boobs using rice and pantyhose.
It escalated so quickly. I went from only wanting to wear pantyhose to suddenly wanting to look and feel like a woman.
She later bought me a French Maid outfit.
She has since moved to another city and I no longer dress up. I purged everything but I still wear pantyhose every single day.
Last edited by Bianca Fay; 08-20-2025 at 07:49 AM.
Hard to recall the exact start. When I was 5, and mom was expecting with my soon to be baby sister, we moved into a slightly larger house. It was still officially only two bedrooms, and initially her cradle went into my bedroom. But my parents swiftly relocated the laundry machines out of the basement laundry room and into a basement 'party room', and converted the former laundry room into a very nice bedroom for me. I had privacy, and my own 3/4 bathroom (toilet, sink and shower, no bathtub). It wasn't long before I took advantage of being very close to the laundry, where I could satisfy my curiosity about mom's clothes! Of course, nothing really fit, but I loved the feeling of her silky slips and half slips on my bare skin - particularly when still warm from the dryer! And being on my own in a basement room made it easy to 'borrow' some of mom's lipstick to try on myself! I'd seen her apply her makeup plenty of times, and got quite a thrill from seeing my own lips red like hers.
By age ten, I had a definite preference to play indoors with the neighborhood girls, rather than play rough and tumble games outside with the boys. I was very confused and hurt when my female friends parents insisted I was 'too old to play like that with their daughters'.
Growing up, the male role never quite felt right. I certainly was never very successful at dating, in high school. (Turns out I was needing a very different sort of relationship, with me in the feminine role, but I didn't figure that out for many years.)
In my 20's, I did what was expected of me, and married a nice girl. But though I agreed to a monogamous, straight relationship with her we both knew I was, at the very least, inherently bisexual. I just refused to explore it further than that.
As a young adult, I found myself increasingly attracted to assuming female roles in roleplaying games. And as those games became on-line play rather than friends around a gaming table, the other players, who had never seen me in person, were quite certain I was a cisgender girl. And I didn't want to correct them on that assumption.
However, I refrained from exploring my femininity in real life until I was in my early 50's. First with covert underdressing, and later, after my wife passed away, by going out publicly as a woman.
11 years after my first steps in public crossdressedcas a woman, my medical transition to fully female is now almost a year and a half behind me!
Last edited by Ceera; Today at 01:22 AM.
I started at around 4 or 5, there was this velvet dress I was just drawn to, I remember even at that young age, that boys weren't supposed to wear dresses, but, I just had to try it on, I got caught by my older sister who of course called my mom and other sister, I hid under the bed and took it off, and wouldn't come out, they teased me a little, but, not in a mean way. I remember feeling so embarrassed. It was never mentioned again and afaik they never told my Dad or two older brothers.I shared a room with my sisters until my early teens - not sure why I didn't share a room with my 2 brothers as they had a bigger room- I didn't really dress up again until my teens, I had access to all my sisters clothes, so any chance I'd get I'd try something belonging to them. I even got to try on both of their wedding dresses. In my teens I often fantasised about waking up as a girl getting to wear all the cute outfits that I saw on girls my age, while other boys would stare at girls to ogle them I'd be looking at their outfits and wishing I could wear them. I never got caught again after the first time as I was extremely careful to only dress up when I knew no one else was around and was very careful to make sure I didn't damage the clothes and left everything back as I got them.
Last edited by Jasmine23; Today at 05:55 AM.
You had a wonderful Mom who encourage you into becoming the girl that you are today. You should be very thankful.
You will become stronger in the ways of the Pink Fog. May the Pink Fog guide you and be with you now and forever.
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