When & How Did You Start to Cross Dress?

I’m interested in when and how people on this site first started to cross dress? Were you a late starter or did you get into panties (pun intended) at an early age? How did it come about?

I well remember the first time I cross dressed. I must have been about 9 or 10 years old. I was invited to a fancy dress party along with one of my female cousins (I was an only c***d) and money being tight our mothers’ decided I should go dressed as a St Trinians’ Schoolgirl wearing the uniform of one of my older cousins. I adored the feel of the stockings on my legs, the garter belt round my middle and the satin smooth panties tight against my cock - which of course immediately got hard. I was quite used to that as were my cousins who had always been captivated by my “extra bit”. They were five sisters with no brother so I was an object of interest which was fine by me. My cousin went dressed in my school uniform as “Little Tommy Tucker” who was a British cartoon character of the time. I really enjoyed myself as did a number of curious little girls. Shortly afterwards I began investigating and wearing my mother’s lingerie. The rest, as they say, is history!

I hope you will feel able to satisfy my curiosity and tell me about your experience.

Love and kisses
发布者 daviea9
11 年 前
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39
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05911010 6 年 前
I really like your profile and your stories. I just found this very old post of yours, but I answered the question a few weeks ago without realising you’d asked it. You can read it here: https://xhamster.com/posts/844801
回答
daviea9 出版商 6 年 前
Loveitall66 : Seems you were a late starter then. Buy hey, better late than never?
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Loveitall66
Loveitall66 6 年 前
I don't remember actually trying on lingerie until I was married with kids (although I'd always had a thing for sexy underwear) I suppose in my early thirties, I'd wear my wife's stockings, suspenders and panties when she was out and under my clothes sometimes. After we split she left some of her stuff and I did it more often and bought some of my own.
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daviea9 出版商 11 年 前
michaella_cd : No, once hooked you are hooked for life!
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daviea9 出版商 11 年 前
LacyNylons : Thanks so much for that information. I shall store it away with all the other interesting (but possibly useless information. I never knew that. Great.
回答 原始评论
daviea9 出版商 11 年 前
l_decal : A close call - but I bet that excited you.
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michaella_cd
michaella_cd 11 年 前
Started at a very early age, I'm guessing 4y/o. I was being bathed by my mum and when she got me out of the bath she had to answer the front door, so she wrapped a towel around my waist and went and answered the door. So there I was for all intents standing there in nothing but a skirt! I wanted to be a girl and cried for days when i found out I couldn't be :frowning:
So from then on until mid teens I dressed in whatever I could find. Then came my future wife and I didn't dress for a few years. But as we all know this cross dressing never ever goes away does it :wink:
回答
LacyNylons
LacyNylons 11 年 前
daviea9 : The boring answer is that women's buttons on hand made clothing for rich people were reversed by the upper classes because they all had ladies in waiting who would dress them. Made it easier for the servants to do them up from the 'wrong' side. After that it was just adapted for all women's clothes and women just got used to doing them up the wrong way. I have to say that after a few goes, it's no harder than doing them the male way around.
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l_decal 11 年 前
My very sexy cousin came to spent some days at my parents place when I was 7. She was tall, long legs, blue eyes, delicious body, extremely attractive woman. When she was talking with my parents at the living room as she arrived I decided to take a look at the room she would be sleeping and found her open suitcase. Inside it I found a very sexy laced white thong, as I took it in my hands I could no more control myself... When I noticed I was already lowering my shorts and trying my first pair of panties! Just an important detail, when I calmed down few minutes later but still wearing her panties I realized that I did it all with the room´s door wide open!
回答
rita43
rita43 11 年 前
daviea9 : thank you xx
回答 原始评论
daviea9 出版商 11 年 前
rita43 : I bet you look good in them too!
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rita43
rita43 11 年 前
daviea9 : black cotton with lace either side hileg ones
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daviea9 出版商 11 年 前
cumulator : Fair enough. I've just be watching your "Wanking in White" video again. Very arousing.
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daviea9 出版商 11 年 前
rita43 : And what colour/material are they?
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rita43
rita43 11 年 前
daviea9 : im wearing bra suspenders stockings panties and a dress today
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cumulator
cumulator 11 年 前
daviea9 : No, neither of them knew/know. It's my little bit of horny fun & all the better for being secret. :smile:
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daviea9 出版商 11 年 前
arnold11195 : Think of Robert Bruce and the spider. If at first you don't succeed try, try and try again. Why not say "darling, sorry about that but the feel of such sexy material was just too much to bear. Maybe if I try wearing sexy undies more often, perhaps even under my outdoor clothes, I'd get used to it. You would get the benefit of my arousal after I got used to the feel a bit more."
回答 原始评论
daviea9 出版商 11 年 前
LacyNylons : Yes, but I was basically wearing a school shirt with buttons the wrong way round. Didn't feel any different material-wise. I wonder why and when it was decided men and women should have buttons on opposite sides?
回答 原始评论
LacyNylons
LacyNylons 11 年 前
daviea9 : I hope my friend's mum was getting some enjoyment from fantasizing about me in her panties, I certainly was! I'd have loved to wear my cousin's panties and blouses. The wrong way buttons has never bothered me. I just love the feel of a soft sheer blouse, especially with a pretty bra underneath.
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arnold11195
arnold11195 11 年 前
Once, a few years ago, wife and I were in bed, she used to sometimes dress up in a teddy. She suggested that I should try it on.... we are both really turned on, I slid it up, slipped into the shoulder straps....... and came in it!!! That was the end of that!
回答
arnold11195
arnold11195 11 年 前
daviea9 : The temptation is there, but no opportunity yet....
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daviea9 出版商 11 年 前
LacyNylons : What a dreadful woman. I'm sure your friends mum knew but she probably had no intention of "getting physical". No, I think she probably fantasised about it.

Apart from what I've written above, I quite often wore girls panties to school. My late father was very ill from time to time and sometimes had to be taken to hospital as an emergency. When that happened I would be taken to my aunt's house to stay and with no clean clothes usually ended up wearing some of my cousins' panties and sometimes had to wear a blouse in place of a my shirt. I hated that part - the damn things button up the wrong way! But I didn't mind the panties at all.
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daviea9 出版商 11 年 前
rita43 : I too underdress daily, sometimes just panties but often I wear hold-ups or even a garter belt. Feels good. I'm wearing some black cotton panties today. Fairly plain but with a nice lace edge. Holds me nice and tight. What about you?
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LacyNylons
LacyNylons 11 年 前
daviea9 : My mother threatened to buy me some girls underwear and make me wear them when I went swimming so everyone would see them when I got changed. My relationship with my mother has never recovered. We still don't get on.
I wish I'd been a bit more confident and open as my friend's mum was beautiful. I'd love to know if she knew, and was leaving things for me or if it was all in my head!
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rita43
rita43 11 年 前
daviea9 : although im still in the closet I dress daily under my male clothes and buy my own clothes now
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daviea9 出版商 11 年 前
I'm sure we all know that feeling! I take it you are still enjoying it?
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daviea9 出版商 11 年 前
Gosh. Not sure what to say to that!
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daviea9 出版商 11 年 前
rita43 : And how has that first time developed?
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daviea9 出版商 11 年 前
ms7071 : You lucky boy, being initiated into the pleasure of panty wearing by your wife. Any chance you might share some of your "bedroom" pleasures with us?
回答 原始评论
daviea9 出版商 11 年 前
LacyNylons : Gosh, what stupid parents to threaten to expose you - even if I presume they were not suggesting you dropped your shorts - at school. Nice to know your friend's mum was more laid back and I suppose she had a nice fantasy thinking about you wearing her undies.

Lots of women do seem to be turned on by cross dressers and who knows, maybe if you had been older she might have done something to fulfil her fantasy.

I've just posted a story about my own such experience - "Dressing for Ann". I'm not sure when it will appear as it is awaiting approval so keep an eye out. I think you will like it.
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