Crossdressing Storieslatest

A CD Journey has to Start Somewhere

Crossdresser JourneyHow Paige became Paige: This is my story of when I first felt the starting feelings of what was later to become Paige but back then it was all just innocent fun or dread initially depending if you ask myself or my sister.

We lived in a remote place in Cornwall in the UK, a long way from any town or village when I was a child. I have a mother and a sister called Chloe (actual name). My sister is my twin and she is older than me by about 1 hour or so, as my sister keeps reminding me.

Back when I was about 7 or 8 years old, we lived on a smallholding in the middle of nowhere with only sheep, chickens and goats for company. We went to school, but it was more like 10 kids in a house being taught by a mother of one of the pupils.

Mom never let any of my or my sister’s friend’s round to play or indeed stay over the night. See my Mom was very private and kept herself to herself which she still does to this day.



So most of our time was taken feeding the animals and playing around my home which I and Chloe both enjoyed doing.

My sister was and still is very bossy so she would win at everything by hook or by crook as the saying goes.

One day when I was around the age of 8 and a half years old, she called me into her room and told me she wanted to play dress up. I said OK I will be the sheriff and she could be what she wanted to be. A nurse, if I recall, was her go-to outfit.

She then dropped a bombshell she said she always wanted a sister and not a brother which hurt my feelings, but she quickly changed it to another sister and me.

I recovered quickly after running to my room. I do remember getting upset for a time.



A few days later Chloe said sorry and that it all came out wrong. I said as any boy would say that I was not bothered anyway.

She then said can we play dress up, so I said OK then. Then she went to her wardrobe and pulled out two of her dresses, her nurses play outfit Mom had made for her and her red party dress. She held them up to me and said which one. So, I said she should wear the nurse outfit and I would play the patient.

(This where the seeds of Paige started but again, she would not be Paige until many years in the future.)

She then said the immortal line of “I want you to wear my party dress, as I never get to play with any girls my age”

I was left well in a state of what do I do. Well, I said no way, no way I remember saying it over and over. I retreated to my room shut the door put my chair against it and sat on it for what felt like hours.

I then heard my sister crying in her room and my Mom came up and told me off, thinking I had had a go at here or something like that.



Chloe was quick to say I had not done anything. To that my Mom went back down the stairs and heard the back door shut. I watched as my Mom went out to the far-field to tend to the goats.

I felt bad that I had made my sister cry, so I went back into her room and asked her why she was crying. All she said was all she wanted was to play with another girl but as she does not have a sister then she will never be able to do it. She then said she was going to run away. I panicked at the time and said I would play; she took it I meant to dress up, so she picked up the dress off the bed and held her arm out for me to take it.

What was really strange I recall back then was instead of me saying no way I instead put my hand out to take the dress which I thought what am I doing. Whilst still thinking what I was going on Chloe was in the wardrobe getting bonnet hat thingy and woolly tights out of the draw and shoes from under her bed.

She followed me with them to my room. She put them on my bed and said thanks Paul don’t be long.

I stood there thinking, how did that just happen. I then had a nobody will know moment so I left my pants and tee shirt and socks on and started to put on the tights, grey to black color if I can remember right over my socks. Then I put the shoes on which would not fit. So I took off my socks and tried again. The shoes fitted this time round. Even then the feelings I had was this is weird and why am I doing this.



Next, I unzipped the dress at the back which was a red dress of some description I can not remember the detail of it and pulled it over my head like a jumper. I could not reach the zip so left it open.

Then I put the hat on and checked outside to see where Mom was. She was still in the field. I went into my sisters’ room and she was dressed in a Cinderella costume to which I though thank god she did not give me that but at the same time thinking oh.

She did what I have rarely seen for a long time she beamed which made me feel happy that I had made her happy. She came over and asked me to zip up the back of her dress to which I did for her.



Then the strangest of things happened she turned to me and said it was my turn to which she then grabbed the zip and zipped up the dress that I had on to the top of my neck.

It felt nice and strange all at the same time it was and still is hard to explain today.

We played for what seemed like hours with her cooker pans and shop with till.

Next thing I hear is mom calling us for tea.

I remember telling my sister to unzip the dress for me to which she did not answer. But instead, she just opened the door and went downstairs.

I heard mom call me again, I panicked and tried to unzip the dress, but I could not reach it.



I heard mom coming up the stairs she opened the door and came in she looked at me and said I thought Chloe was telling me porky pies.

Chloe had told mom I was playing dress-up with her. Mom thought It was nice for me to do it for Chloe.

All I heard my mom say was come on lunch is getting cold. I then followed her down the stairs.

We all sat eating out lunch. Then when we had finished mom said to use both to go play outside for a bit.

I found my self herded out the door by my mom’s hand and the door then shut behind us both.

I felt like I needed to hide but it also felt strangely nice.

We played skimming stones on the pond at the side of the house.



I then heard a van noise, next thing the postwoman was in front handing me some letters and saying, “hello girls” and asking how my mother was to Chloe. She said my name was Paige to postwoman, I kept quiet and a few minutes later we were allowed back inside.

I rushed upstairs and Chloe followed behind.

She unzipped the dress for me, and I went back to my room and changed back into my clothes.

I took the clothes back to Chloe’s room and she asked if we could do it again in the future.

I remember saying why not.



It happened two more times after that then it stopped when I was 9. My sister was now more engrossed on the internet we gradually started to do our own things. I found the play station taking more of my time up. We basically grew up and we have never ever talked about it ever since even to this day. It never gets bought up at parties or family gathering. (Good job really)

The story as you know it does not end there as I have taken the name that Chloe gave me back when I was 8 and that is indeed Paige but my sister is totally unaware that those three dressing up days have stayed with me and had an impact on my life today as Paige.

Submitted by Lady Paige 

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1 Comment

  1. J’aurai aimé avoir une sœur qui me demande de me déguiser avec elle . J’aurai trouvé ça normal et je ne me saurais pas posé de questions . J’accepterai plus facilement ce que je vie maintenant .

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