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<p style=”text-align: left;”>When did the desire to crossdress begin for you?</p>
Was 12 or 13 and puberty was not going well. So confused at that time. Until I found boxes and hanging storage closets full of dresses, bras, girdles, nylons, garters and heels. It was like discovering a hurried treasure. From then on I new what my destiny was!!
Lanna💋❤💅👙👗👠👢
For me I was 8 or 9 tried on my mum’s knee high boots, felt something tingle inside, at 11 moved on to her undies, bra, stockings, skirts etc, started buying my own in my late teens, just gets me so excited.
When I was 3 to 4 years old, my mother would apply lipstick and makeup on me when she dressed. She always wanted me to be a girl. At a young age, I had those strong feminine feelings. At 11 or 12, I would play with my mother’s makeup when I knew it was safe. I started dressing later and have stopped and started so many times, but the feminine feelings go to my early childhood.
I can’t exactly remember when except that it was a very young age. Most importantly, I don’t know why. I remember my first time actually doing so though…..
I remember that myself and younger brother were being loud obnoxious little boys chasing each other through the house. At one point, we both ran towards and dove into the massive pile of everyone’s laundry waiting to go into the washer and dryer. After we got done laughing, he got the idea to dare me to put on one of my mom’s shirts (T-shirt…nothing special). I did and we went back and forth taking turns daring each other to put on a random clothing item for us to laugh at. Just shirts and pants at first….us as very tiny kids wearing full size adult clothes over our own clothes. By the time we heard our mom yell at us from another room to get out of the laundry room, we quickly piled up the laundry again. Before he ran out of the room ahead of me, I saw him grab one of my older sister’s 2 bathing suits. Knowing what his plan was since it was his turn to dare me, I grabbed the other one and chased him into our shared bedroom. We continued the dares, and I pretended that I did not want to put that on even though I was screaming “hell yes” in my mind. We then settled on just putting one on at the same time after a little arguing…and to ensure that one could not make fun of the other one about it later. We put them on. The one I was wearing fit perfectly…leading to my current addiction to want to always wear one. I think we had them on for about 10 seconds before taking them off. Knowing that we could not sneak back into the laundry room, we hid the swimsuits under our mattresses before going outside to play. Our argument out there became a matter of who won because of who took the swimsuit off first. Then the agreement of a rematch was on. That evening after we were supposed to go to sleep, we took the swimsuits, put them on again, then waited to see who would be the first to take it off. I think we got a minute into it before he took it off. I pretended to make sure “I won” by sleeping in it.
I always wonder where the desire comes from, for me it was the feeling of being pretty, I always found girls pretty and boys ugly and I want to be pretty, I still feel that way, whenever I see a girl in a nice dress I want to look like her, or to feel sexy in lingerie, there was a sex connection at one stage but now it is more to do with feeling attractive and sexy.
I was about 10 years old, in 1960, and I got excited when I looked at Betsy McCall, the paper-doll girl, in her undies. I was even more excited when I realized I could look just like a pretty girl if I had long hair, wore girl’s undies, and hid my “little something” between my legs. By the time I was 11, I admit, I sometimes pretended I was a naked girl, but I also desperately tried to look like a girl with little breasts by stuffing wadded-up hankies under my sweater. I had no sisters, my mom’s undies wouldn’t fit me, and I had no way to get any girls’ clothes in reality–but I did in fantasy. I drew lots of pictures of myself looking like a girl in different states of dress and undress–and I still do!
Pretty typical I imagine. I was about 12, alone in the house. I was masterbating and having the house all to myself, I seemed to be searching for something to make things more exciting. I went into my moms drawer and tried on her satin panties and pantyhose.
just found myself in my parents bedroom at age 11 or 12 when they were out somewhere and starting putting on mom’s bra, girdle and nylons and it has never stopped
my actual crossdressing came about as a consequence of my interest in BDSM and my Mistress decided to feminize me and make me Her ‘sissy bitch’. From that moment on i have been more and more interested in complete crossdressing outside of BDSM. Thinking back to my early adolescence though i recall being very excited in the women’s underwear section of the Seat & Roebuck catalog and imagining myself forced to dress like that. Apparently i was a sissy from an early age who grew into a mature crossdresser
I, too, got excited by looking at girls and women in undies and swimsuits in Sears catalogs; I imagined myself, and drew pictures of myself, looking like them in the same clothes–but nobody had to force me to wear them, and I wasn’t going to let anybody force me not to wear them!
i have always been submissive and my fondest dreams involve serving a demanding Mistress. i suppose some may stem from dealing with the guilt and shame society heaps on crossdressing males especially in the sixties and before. After all if you are being forced it is not your fault and there is no guilt. Sadly it doesn’t work perfectly because you realize whether you obey your Domme is still your choice
Lisa
we all have moments that defined our transition. Suffice it so say, without too much detail, that early in my evolution I did not even recognize those X-Roads. If someone were to review the film of my life, there were telling moments that this Question Post has brought to the surface. Perhaps in time I can gather those words together…
I have seen photos of myself as a three year old wearing what looked like heavy stockings held up by garters. I was wearing very short shorts and had a bobby pin in my hair. I guess boys wear dressed like that in Europe back then. However I don’t remember it.
When I was about six or seven my aunt dressed me in her dress, kitten heel shoes and earrings. I remember really enjoying it. My mother was there and didn’t object and when my aunt went home she left the shoes and I would wear them whenever I could. That is the earliest I remember dressing.
like many it seems, as a young boy i would try on pantyhose and love them.
as the years passed, i would see a cd or tv in public, movies, wherever and get very excited. wondering what it was like, what their lives were like, how it felt, etc.
many starts, stops as the years passed. finally, as an adult, i asked the guy i was seeing if i could wear pantyhose for him. he agreed. one of the most thrilling nights of my life ensued.
from there, i quickly went to the near full-on – wigs, lingerie, some makeup. never breasts though. not interested in that.
I was 5 or 6 and my Aunt was 22ish and we shared a room and a dresser…. She never mentioned her things being rifled through…. That’s my first relevant memory. The real desire however is much more recent. I started with Panties 5 years ago. For the most of that time playing with the Idea of dressing. For the last year and a half. Wanting to dress and dabbling with a few items. Now, strong desire to dress fully.
-Autumni was much older than the most others here i see.
Im bi so my first time was with a man who wanted me to dress. it was just some lingerie. i was around 30 and i did it some times moore after that but i think i was afraid of my feelings so i stopped, then i meet my wife. but i couldnt stop thinking of it so a few years ago i started to dress again but just for myself. i bought wig makeup dresses highheels and realized that it is a part of me and i have a need to entertain my feminine side to feel well.
I began wearing pantyhose with pumps and a shirt that looked like a short dress when I was 4. I began buying my own pantyhose at 13. At 17 I wore pantyhose out with guy shorts and clothes. Then I decided I needed a better look. I bought some short girl’s shorts and some platform wedges.
The pantyhose and shorts I could keep hidden among other clothes. The wedges I kept stashed in the trunk of my car. When I was 18 I got my own place and really began upping my fem warrobe.
I think it was watching my mother put on her stockings when I was three started me on the road to want to dress as a girl.I tried in vain to put on stockings when I was about six to no avail.My first real experience was when my girl cousin five years my senior dressed me up as a girl with makeup sadly no pantyhose when I was ten years ago.My first successful closeted experience was wearing my mum’s tights.No other female clothes were accessible wore them with a boys tank top and wore my gym shorts as hot pants.A case of partial dressing but I felt girly enough.Was so plessed that the tights fitted me and was quite pleased with the shape of my young legs despite being short in stature
When I was about 14 I saw a TV show about a man who dressed as a woman. He looked great. I was excited! At this time of my life I had long hair and was small for my age. I was mistaken for a girl several times. An opportunity arouse that I would be home alone all day. I took the opportunity dressing in my Mom’s and sister’s clothes. I realized then how much I enjoyed it.
In second grade I was the only boy in a piano recital. I wore a little boy’s suit and sat between girls in dresses with petticoats. We were seated very close together and I loved the way their dresses and petticoats felt on my legs. I wished I was wearing what the girls were wearing. In the car on the way home I was going to tell my parents–being an innocent little kid–but something told me not to, to keep it to myself. So I did and have ever since. I’m now 60. Imagine that. Twice at parties when I was in my twenties I somehow ended up letting women put lipstick, rouge, eye shadow, etc, on me. I can’t really explain how that happened twice, but it did, and both times woke up the next morning and was thrilled to see my face made up. But I guess that’s another story. Anyway, I repressed my fondness for women’s clothes until a few years ago. I wear women’s clothes and sissy clothes at home, never in public.
I was 5 the first time I dressed. My older sis (by two years) and one of her friends put me in an old sundress of hers with panties and sandals so I could play Barbies with her and her friends and not get arrested for being boy and playing with girls dolls. Didn’t every child know that it was aginst the law to do that, according to one of the older girls in my sisters group, lol. Never looked back since then.
Paula
<p style=”text-align: center;”>I was 4 or 5. It must have been around the holidays as my younger sister was wearing a pretty dress with white tights. For some reason I wanted to know what the tights felt like. So I asked her if I could. As I was struggling to get into them my mom walked in and yelled “STOP!! You’ll ruin them!” She told me if I wanted a pair of tights she’d get me a pair of my own. A few days later found us at Baum’s Dancewear store in Philadelphia and she walked me up to the sales girl and said “A pair of tights for the boy.” I was really embarrassed somehow but covered by telling her I wanted organge “cause that’s what Captain Marvel has.” So that was my first item of girl’s clothing, orange Danskins. We got them home, I guess Mom showed me how to put them on and I’ve been a goner ever since. When I started wearing Mom’s other things around 11 or 12 I went underground with it. Still trying to claw my way into the light all these years later. But that’s how it all began for me.</p>
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