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Where did it begin?

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(@Anonymous)
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<p style="text-align: left;">When did the desire to crossdress begin for you?</p>

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Lady
(@sammatha)
Reputable Member     BELFAST, County Antrim, United Kingdom
Joined: 6 years ago

In my early teens to b honest.

Stopped for a while. Bought lovely underwear as a student. Asnd developed from there. Just live cdh. Its a supee place

Love sam x

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Posts: 371
(@oldybutgoody)
Reputable Member     Coventry, Warwickshire, United Kingdom
Joined: 6 years ago

I found boxes of brides maid dresses at my grans house, I was nine or ten, of course I tried them on and even remember tying myself to a table leg and waiting to be saved?

Was it cross dressing or just a lonely childs dressing up game?

 

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Posts: 556
Lady
(@lannab)
Honorable Member     Allentown area, Pennsylvania, United States of America
Joined: 8 years ago

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💋❤💅👙👗👠👢

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(@Anonymous)
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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.

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(@Anonymous)
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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.

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Lady
(@kmsmst)
Honorable Member     South of Omaha, Nebraska, United States of America
Joined: 6 years ago

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.

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(@Anonymous)
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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.

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Lady
(@kmsmst)
Honorable Member     South of Omaha, Nebraska, United States of America
Joined: 6 years ago

Like I said, the interest in swimwear was there already. No idea why. That story was just how I actually first did it.

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(@dulci)
Eminent Member     Indiana, United States of America
Joined: 6 years ago

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!

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(@Anonymous)
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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.

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(@Anonymous)
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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

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Lady
(@bobbie1951)
Reputable Member     Homosassa, Florida, United States of America
Joined: 6 years ago

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 

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(@Anonymous)
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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...

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(@dulci)
Eminent Member     Indiana, United States of America
Joined: 6 years ago

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!

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