How did crossdressing start with you all?

[Andy86]

When I was about 12 I started wearing my older sisters knickers, bras, skirts etc knickers are just so much better than boxer shorts

 

[ozzy4605]

When I was about 12 I started wearing my older sisters knickers, bras, skirts etc knickers are just so much better than boxer shorts

That thay are, there just like the boys brefs that i wear now, as like you i did wear my younger sisters panties and other girls clothing, and i think my sister was wearing my clothing as well, if i had of court her wearing my clothes then we could have swoped genders and rooms with our mothers approval, sadly i never did catch her, it would have been the best thing ever.

 

[Anemone]

Its nothing you could control at that time, it was set into your brain as you were forming inside your mothers womb, if your mother gets a rush of female hormones, as your brain is forming then it might be wired up to be like a girls brain or a partial girls brain, if your mother gets a female hormone rush late in your brains formation, that might be why you like to dress in girls clothing.

That sounds extremely speculative and reductive.

Granted it is certainly not anything under conscious control, that much is a truism.

 

[Ali123]

When I was about 12 I started wearing my older sisters knickers, bras, skirts etc knickers are just so much better than boxer shorts

How much older than you is your sister?

Did she ever catch you in her clothes?

 

[ozzy4605]

How much older than you is your sister?

Did she ever catch you in her clothes?

My sister is 1 year younger then me, and no she never corte me, but i did catch her in my clothes twice, once wen she had a frend sleep over, her frend daird her to wear my clothes, then my sister daird me to wear her frends clothes i did wear them, it was what my sisters frend was wearing at the time, me and my sisters frend went into the bathroom to change clothes, just took all our clothes off and we were standing in our underwear, and i sayd i think we should go all the way as we have come this far and she sayd ok, there we were both naked, i think i sayd you look nice or something like that, then we got dressed, my sisters frend put my underwear, shorts and tee shirt on, then she helped me get her underwear on, and then it was her white care bears button up top and her pastel pink care bears shortalls on, then it was out to show my sister, she was stuned that we looked like twins, we stayed like that for over 2 or more hours then we changed back into our own clothes with one exception, i kept her underwear on and my sisters frend kept my underwear on, then the second time i corte my sister wearing my clothes was, when the washing machine broke and she ran out of clean everyday clothes, i let her off that time.



This is something like the shortalls my sisters frend was wearing at that time, hers had the care bears on them,
not the care bear cousins like these have on them, but you get the idea.

Care bear Official dungaree shorties

S$85 | Tag says size Medium; fits UK10-12, IMO. For the young at heart.. adulting is tough isnt it? LOL!

www.carousell.sg

 

[Deleted member 75402]

My sister is 1 year younger then me, and no she never corte me, but i did catch her in my clothes twice, once wen she had a frend sleep over, her frend daird her to wear my clothes, then my sister daird me to wear her frends clothes i did wear them, it was what my sisters frend was wearing at the time, me and my sisters frend went into the bathroom to change clothes, just took all our clothes off and we were standing in our underwear, and i sayd i think we should go all the way as we have come this far and she sayd ok, there we were both naked, i think i sayd you look nice or something like that, then we got dressed, my sisters frend put my underwear, shorts and tee shirt on, then she helped me get her underwear on, and then it was her white care bears button up top and her pastel pink care bears shortalls on, then it was out to show my sister, she was stuned that we looked like twins, we stayed like that for over 2 or more hours then we changed back into our own clothes with one exception, i kept her underwear on and my sisters frend kept my underwear on, then the second time i corte my sister wearing my clothes was, when the washing machine broke and she ran out of clean everyday clothes, i let her off that time.



This is something like the shortalls my sisters frend was wearing at that time, hers had the care bears on them, not the care bear cousins like these have on them.

Care bear Official dungaree shorties

S$85 | Tag says size Medium; fits UK10-12, IMO. For the young at heart.. adulting is tough isnt it? LOL!

www.carousell.sg

I love it that you both stripped off and swapped underwear too.. so sweet that you said she looked nice ... I bet it felt so nice wearing her knickers straight after she had slipped them off and so lucky for being able to keep them on afterwards.. lucky boy

 

[ozzy4605]

I love it that you both stripped off and swapped underwear too.. so sweet that you said she looked nice ... I bet it felt so nice wearing her knickers straight after she had slipped them off and so lucky for being able to keep them on afterwards.. lucky boy

I was lucky at the time, and i think my sisters frend secretly liked me, and i did like her but was to shy to say it.

 

[Deleted member 75402]

Oh If you had been not so shy you could have been very naughty...

 

[StrawberryPan]

I've been kind of thinking about this alot lately. I can trace things back to two events in my life, though I'm not sure which actually came first.

When I was growing up we would often go over my cousins' house for holidays. They had a really big family, and these cousins were almost all girls, except for one boy they had but at the time when I was a kid he was basically a baby so when we were ushered down to the basement to play it was just me, my girl cousins, and whatever girl friends they had over at the time. The oldest was around 14 when I was 6ish and the youngest was my age. So, they played like girls do, and loved having me over so they could play 'school' with me as the little student and them as the teachers. Somehow this evolved into them having me wear their clothes, undies and all, and playing school as a little girl. I would be given tests and if I didn't do good I would get corner time, also during 'recess' they expected me to do girl stuff and play house with them as one of the girls, and like, dolls, 'tea time' (lol) and stuff like that. I would pretend to hate it and protest but I was totally outnumbered and I secretly loved it lol. There was also a huge trunk of random costume stuff down there, all girl stuff ofc, so sometimes we would play dress-up which inevitable evolved into them dressing me up in ridiculous princess outfits and stuff. I think I had a very good childhood, lol.

Around the same age I discovered a whole trunk full of kid-sized girl's clothes in our attic, so my new favorite game became trying them all on and playing by myself like I was a girl. I still have no idea why we had those clothes up there, my parents got rid of them when I was around 12-13 or so and I remember I was pretty much devastated by it but I couldn't say anything. Around then was when I started getting much more into diapers and stuff, and I can't help but think there is some relation there.

 

[ozzy4605]

Oh If you had been not so shy you could have been very naughty...

Me at 8 years old and my sisters frend at 7 years old, i don't think we even knew what naughty was back then, but i can rember that she was a hugger not a hanger, that just meens that her outer visible girls bits hug the boddy like a barbie doll (a hugger) or hang down a little bit like a wet saggy nappy (a hanger).

 

[Deleted member 75402]

Me at 8 years old and my sisters frend at 7 years old, i don't think we even knew what naughty was back then, but i can rember that she was a hugger not a hanger, that just meens that her outer visible girls bits hug the boddy like a barbie doll (a hugger) or hang down a little bit like a wet saggy nappy (a hanger).

Sorry didn't realise your ages

 

[ozzy4605]

Sorry didn't realise your ages

Thats ok, theres nothing we could have done at the time anyway.

 

[Andy86]

How much older than you is your sister?

Did she ever catch you in her clothes?

She is 2 years older than me, and no she never caught me in her clothes

 

[ozzy4605]

She is 2 years older than me, and no she never caught me in her clothes

You must have been one very sneaky boy.

 

[StrawberryPan]

You must have been one very sneaky boy.

And lucky. My entire life growing up I wished I had a sister so I could borrow her clothes lol >_<

At least I was lucky enough that by brother was a bedwetter so I got to """borrow""" his pull-ups lol.

He still would have made a better girl, but he will never realize that. Long story.

 

[Andy86]

You must have been one very sneaky boy.

Yes indeed, I often wonder if she knew though as maybe her knicker drawer was a bit messy after I had been taking her knickers to wear

 

[annie]

Its nothing you could control at that time, it was set into your brain as you were forming inside your mothers womb, if your mother gets a rush of female hormones, as your brain is forming then it might be wired up to be like a girls brain or a partial girls brain, if your mother gets a female hormone rush late in your brains formation, that might be why you like to dress in girls clothing.

maybe we will never know. all i know is i was never a male as males go. even when i was younger i would talk my sister old studd and hind it. i would wear girls underwear and tights under my boy clothes even to school well until i was caught.

 

[Ali123]

She is 2 years older than me, and no she never caught me in her clothes

That’s a shame. Older sisters can be quite mean when they catch their little brothers wearing their panties.

 

[ozzy4605]

That’s a shame. Older sisters can be quite mean when they catch their little brothers wearing their panties.

I hope she let you keep one pare of tights and one pare of her underwear, to stop you from going thrue her stuff.

 

[treehopper]

He still would have made a better girl, but he will never realize that. Long story.

Why would he make a better girl - Is he very girlie ? small dingle ? effeminate ?