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
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
11 years ago
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
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.
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!
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.