My first memory of crossdressing

My first memory was me and my brother mucking about and him having the idea of putting on my mums nightwear.

I must have been maybe 5 or 6? And I vividly remember wearing a satin night gown and satin dressing gown.

We were laughing and joking and showed my mum, she of course told us to stop playing about with her stuff and take it off.

But I remember looking down on myself and feeling that fabric on my body and it sparked something in me, I believe this was the exact point of my crossdressing journey.

From then I started sneeking in there at moment I was alone to try on those gorgeous short nightgowns. I love the feel and the colours, it felt like a soft liquid flowing over my skin. I knew boys don't wear these things but I was compelled to carry on.

I want to share my origin with my first post and over time go through the years of memories.

It starts here and then goes into how my mum used to iron clothes for people for money and always having new girly items to try on, to her finding stashes but not really confronting me about it and to the time she gave all my items away to charity and me hidng items under my bed and her placing them on my bed to kinda let me know that shes knows in an odd way.

Then Halloweens of dressing as a girl too many times that people started questioning me so I had to lay off the "female" side of Halloween.

One of my friends gf's giving me clothes she no longer wanted knowing I was crossdresssing but kept my secret.

I also came up with an idea sell clothes on ebay and make it normal for me to ALWAYS have girls clothes in my room.

If you would like to hear these stories please let me know, and if you had any similar situations please write it in this thread.

Thank you all for taking the time to read this and I'm very happy to finally share my experience.

Thank you for sharing - my origin story is simply my trying on my mom's lingerie and skirt suits when I was 13

I can totally identify. My first experience aLeo occurred around 5 or 6, except my first try-on were nylon stockings. The pleasure I experienced was overwhelming and has continued to be my #1.

Stockings, leggings and tights are amazing to wear. Slipping them onto your legs for the first time is an overwhelming experience.

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You're welcome, and thank you for reading. Love pretty lingerie and I haven't worn many ladies or girls suit sets. I do really enjoy wearing midi skirts or tight fitting lined office skirts.

Sorry, it's easier to say I just love to wear anything femme!!

Thank you for sharing and Welcome. Id love to hear your stories especially how the selling clothes on ebay went. It seems like a great idea to cover crossdressing

Welcome,
You are certainly not alone. Many of us started by wearing our mothers pretty silky lingerie.

Definitely my first clothing worn was my mother's lingerie.

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Originally Posted by kinky_caitlin

Thank you for sharing and Welcome. Id love to hear your stories especially how the selling clothes on ebay went. It seems like a great idea to cover crossdressing

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Amazing cover! And it's still going strong, I had a bit of a break from it and purged, but I'm back at it again now, I get tons of new items in and keep what I like and what fits me well and sell the rest! I have so many girly clothes now more than ever!

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Originally Posted by alwayshave

Definitely my first clothing worn was my mother's lingerie.

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For me it was the colours and the fabrics, I always thought why can't I wear stuff like this as a boy?? It's just a piece of cloth.

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Originally Posted by Lacey New

Welcome,
You are certainly not alone. Many of us started by wearing our mothers pretty silky lingerie.

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I was never encouraged, but I'm 99% sure my mother knows, probably does not like it but ignores it. I think.......

My 1st experience was my mothers tights. Things developed rapidly from there.

Having no crossdressing experiences as a child or teen, my backstory is a little different. At age 28 I put on my wife's nightgown as kind of a joke. After we both laughed, she asked if I liked it. I said no.

I lied - and now it's all this!

When I was younger with no internet or cell phones we were forced to do different things as children. I had a lot of girl cousins and we would play board games and do little plays or mini shows and perform for our parents. On more then one occasion they would dress me as a girl and at times I thought that was maybe the spark. But for some reason my greatest memory of my first time was sharing room with my slob sister and one morning there were a pair of beige pantyhose hanging on my bed post. My curiosity got the better of me and I tried them on and let's just say fireworks went on in my head and then I knew this was going to be the beginning of a long relationship. It didn't take long before I picked up one of the many slips that were on the floor and that was an amazing combination with the pantyhose. The funny part was one morning I thought she went to school and I put her pantyhose on and was going to town with them when all at once she came back in the room looking for those pantyhose. She asked me if I had them and started pulling my sheet demanding them back, I don't know what she thought I was doing with them but when she finally pulled the sheets off me she stood there dead frozen seeing me full erected wearing her pantyhose. After what seemed like eternity of her staring at me she threw the sheets back at me and told me the pantyhose are mine now. The funny thing is she never mentioned it again and sure didn't stop trying to be neater and keep them away from me, almost like giving me a green light to them in which I definitely took advantage of. Thanks for letting me have these flashbacks and enjoy your journey.

Hi Pam :hugs:, We have so many great Memories into the world of Crossdressing, >Orchid**O:daydreaming:O**

13 with my mom's romantic lingerie, and I've loved and been obsessed with beautiful lingerie ever since!

Hi Pam,
I've told this before, so will keep it short. I was 4 or 5 and their was this velvet dress I just felt an overwhelming urge to try on, got caught ( first and last time), but, was hooked from there, didn't really start dressing up again until my teens, but, my fist experience at 4 or 5 was the one that got me hooked.

Would love to hear more about your crossdressing adventures.
BTW have you ever wondered if your brother continued to dress up?

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Hi Maria,

Interesting story regarding your sister, was she older or younger than you and what ages were you when she caught you. I also shared a room with my 2 older sisters until I was around 11, so I think this definitely influenced me and set me on my crossdressing journey.

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Originally Posted by Jessica Secret

13 with my mom's romantic lingerie, and I've loved and been obsessed with beautiful lingerie ever since!

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What drew you to it in the first place? From my story you can tell it wasn't my idea but the sensations took over and got the better of me.

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Originally Posted by Kris Burton

Having no crossdressing experiences as a child or teen, my backstory is a little different. At age 28 I put on my wife's nightgown as kind of a joke. After we both laughed, she asked if I liked it. I said no.

I lied - and now it's all this!

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So you qore the nightdress and thought this is actually really nice to wear! We have hardy any options as a man, when you go into the world of women's clothing you realise how much choice there is!

While I may have dressed earlier in life, like maybe playing dress up with my older sister when I was really little, my first true cross dressing memory came when I was 13 and I still remember it vividly.

It was the first week after school let out and I had enjoyed sleeping in. I went to the bathroom and was sitting on the toilet. All the kids in our family shared a bathroom. My sister, who was 2 years older than me, had left a pile of her clothes on the floor. On top of the pile was her panties ... white cotton briefs with little blue flowers. I remember reaching down and picking them up. It was like a magnetic attraction. I remember wondering what it would be like to wear them and feeling like I absolutely HAD to put them on. I kept thinking that, on the one hand that would be too weird but, I just had to do it. I was sitting there hold them in my hand, frozen for what seemed like several minutes thinking I really needed to put them down.

Finally, made sure the door was locked, pulled them on, and looked at myself in the mirror. To this day I still haven't settled on a word to describe how I felt. It was a mixture of joy, excitement, a little sexual arousal, a bit of fear that someone would ever find out. Being a 13 year old boy, arousal won out.

Afterwards, I quickly pulled off the panties and put them back on the pile, hoping nobody would notice I had touched them. All I could think of was that someone would know and tell everyone that I was a queer or a pervert. I would get teased mercilessly and probably get beat up if anyone knew. I promised myself that I would never do that again. Of course, we all know how that worked out!!

I was 12/13. I was curious about what it was like to wear a bra and loved it. Tried on some more things and that was that.

Oh the times my mum caught me in her clothes. Alas the sentence / penalty was always passed to my dad to implement. Ouch!!!

my first memory was when I was 8 or so years old. I was in competitive artistic roller skating. One of the outfits was white and you could see my underwear. My mom, and my partner, had the idea to put me in white dance tights. My mom dressed me, but once I got them on, the feeling was exciting (feelings and physically). That was the end of that idea of theirs, but the beginning of my wanting to wear female clothes.