I Remember My First Crossdressing Experience
First crossdressing memories
I originally posted this over two years ago and deleted it when I decided to remove myself from EP, however I have now reincarnated and decided I will share again with you my ‘foundations’ into crossdressing.
My very first memories go back to when I was probably about 10 years old. I remember that my parents had gone out for the evening whilst I was left at home being looked after by the girl who lived across the road and her boyfriend.
I had noticed, even at this early age, that she was stunningly attractive, a look upon reflection similar to Audrey Hepburn. I remember she used to wear tight skirts and jumpers that showed off her conical breasts and she always had dark seamed legs. She wore her hair in a wonderful beehive and she trailed a flowery fragrance as she walked past you. The night they came to ‘babysit’ I could not get to sleep for thinking of her being in our house, so close downstairs, watching our old black and white TV with her boyfriend. I decided to creep down the stairs and see if I could have a peek at her from behind the lounge door. As I started to carefully make my way down the stairs I noticed the lounge door was half open and I could see her and her boyfriend on the settee, with their backs to me, and what a sight I saw. I can still see it after all these years! They were snogging passionately; she had her skirt up around her hips with her legs slightly splayed apart, showing stockings and suspenders, his hand was down the front of her panties. I sat there for what must have been ages whilst strange feelings were stirring in my willie department. I eventually crept back upstairs after they pulled apart and she had tugged her clothes back into place.
Back upstairs in my bedroom the sight of her and her underwear had taken over me and I had the strange idea that I must try on some of mothers just to be like the girl downstairs. I remember the feelings in my willie were somehow connected to the underwear and overwhelmingly forcing me to do this, but it also felt so wrong! Nevertheless, I went into the bathroom and took out a suspender belt and a pair of nylons from the wash basket, returned to my bedroom and put them on. They were far too big for me but I managed to shorten the suspender belt by using the safety pin that I found in the front of it (I found out some time later that the safety pin was used to secure a Dr Whites in place, but that’s another recollection to write up!) The feeling was electric and my young body was shaking with excitement. I remember franticly squeezing and squashing my willie until waves of relief poured through me. I was pre pubescent so ejaculation was not known or possible, but that feeling I got was very similar to a climax.
I quietly returned the underwear to the basket and went to bed with a wonderful feeling of relief but I was full of guilt as I lay there trying to come to terms with this new experience yet knowing I had done something very naughty that must be kept totally secret to me as no-one else in the entire world would have done the same as me!
That’s how it all started for me. A few more dressing experiments through my teens then regularly from my 20’s. Thank you to the girl from across the road whose name now I cannot remember! but after 50 years I am still secretly indulging in my guilty pleasures as often as I can.
I originally posted this over two years ago and deleted it when I decided to remove myself from EP, however I have now reincarnated and decided I will share again with you my ‘foundations’ into crossdressing.
My very first memories go back to when I was probably about 10 years old. I remember that my parents had gone out for the evening whilst I was left at home being looked after by the girl who lived across the road and her boyfriend.
I had noticed, even at this early age, that she was stunningly attractive, a look upon reflection similar to Audrey Hepburn. I remember she used to wear tight skirts and jumpers that showed off her conical breasts and she always had dark seamed legs. She wore her hair in a wonderful beehive and she trailed a flowery fragrance as she walked past you. The night they came to ‘babysit’ I could not get to sleep for thinking of her being in our house, so close downstairs, watching our old black and white TV with her boyfriend. I decided to creep down the stairs and see if I could have a peek at her from behind the lounge door. As I started to carefully make my way down the stairs I noticed the lounge door was half open and I could see her and her boyfriend on the settee, with their backs to me, and what a sight I saw. I can still see it after all these years! They were snogging passionately; she had her skirt up around her hips with her legs slightly splayed apart, showing stockings and suspenders, his hand was down the front of her panties. I sat there for what must have been ages whilst strange feelings were stirring in my willie department. I eventually crept back upstairs after they pulled apart and she had tugged her clothes back into place.
Back upstairs in my bedroom the sight of her and her underwear had taken over me and I had the strange idea that I must try on some of mothers just to be like the girl downstairs. I remember the feelings in my willie were somehow connected to the underwear and overwhelmingly forcing me to do this, but it also felt so wrong! Nevertheless, I went into the bathroom and took out a suspender belt and a pair of nylons from the wash basket, returned to my bedroom and put them on. They were far too big for me but I managed to shorten the suspender belt by using the safety pin that I found in the front of it (I found out some time later that the safety pin was used to secure a Dr Whites in place, but that’s another recollection to write up!) The feeling was electric and my young body was shaking with excitement. I remember franticly squeezing and squashing my willie until waves of relief poured through me. I was pre pubescent so ejaculation was not known or possible, but that feeling I got was very similar to a climax.
I quietly returned the underwear to the basket and went to bed with a wonderful feeling of relief but I was full of guilt as I lay there trying to come to terms with this new experience yet knowing I had done something very naughty that must be kept totally secret to me as no-one else in the entire world would have done the same as me!
That’s how it all started for me. A few more dressing experiments through my teens then regularly from my 20’s. Thank you to the girl from across the road whose name now I cannot remember! but after 50 years I am still secretly indulging in my guilty pleasures as often as I can.
70-79, M
