Real story that has been a basis of fantasy for years. Would love to hear in comments section if other people have had comparable experiences.
This happened back just about when I was in puberty, I think I was probably about twelve but might have been thirteen.
My mother was never what you call a warm woman. Her love was never shown physically with hugs and things and she was more concerned with us kids behaving well than encouraging us to express ourselves. She had very strict ideas of masculinity and femininity, boys were to be strong and grin and bear things while girls could be more emotional and should rely on men to do jobs for them.
One day I remember being in my room reading a book when she called for me to come downstairs. My sister had found a spider which she hated and Mum told me to pick it up and get rid of it. I was the only man in the house she said and it was my job. The problem was I was even more scared of spiders than my sister. I refused and Mum told me 'don't be silly, act like a man.' I still refused and she yelled at me. Eventually I had to give in, I couldn't take her jibes and yelling anymore and I went to pick up the spider. As I did I started to cry, I was terrified. I just about got my hands around it and felt it wriggle. I screamed, dropped it and just ran to my room where I threw myself onto my bed sobbing.
I lay there alone for I don't know how long. Eventually I regained some composure when the door opened and it was my mother. 'So what was that all about?' she asked quite sternly. I tried to say something but words wouldn't come out and I started to sob again.
'Really! Call youself a man? Your worse than a girl!' She did not exactly shout, it was more of a raised voice.
'Well if you want to be like a weak little girl, then you might as well do it right!' She turned around and walked into my sisters room. In a few minutes she was back, in her hand some of her clothes.
'Undress and put these on.' I just did as I was told. I stripped off to my underpants and reached out for her to give me something. 'Those as well.' She said pointing at my underpants. I took those off as well and was naked, still crying in front of her.
She passed me a pair of my sister's panties. Frilly white ones. Sis was a year older than me but they fitted perfectly, although they were a bit uncomfortable not being designed for a cock and balls. Next Mum gave me what she called a slip, it was really a frilly petticoat designed to make skirts look fuller and also so that nothing showed if tops were too see through. Then she passed me the dress she was holding, it was one my sister hated but mum loved: pink with short sleeves that were trimmed with lace and there was matching lace around the high neck and the hemline.
Finally, I was given two of my sister's long white socks and a pair of her sandles to wear. As I stood before her dressed in my sisters clothes, tears drying on face, Mum smirked. 'Let's see how you like being a girl then. You can wear that until you come to your senses and don't think you can play with your toys either: if you want something to play with you can have some dolls! Now come downstairs and let your sister see you.'
At that I was marched downstairs. My sister went into a fit of giggles as Mum explained this was my punishment for not being a man.
The rest of the day was a bit of a blur, I was given the chores my sister usually had: washing up, ironing, even pegging the washing on the line outside. The last was the worse, the neighbours were in their garden and watched me clearly making comments to each other about me. I avoided their eyes and got inside as quickly as possible. The only saving grace was Dad was away on business so he would not see me.
All through the day Mum would make jokes about me and started calling me 'her new daughter'. The thing was after the intial shock and embarrassment I quickly got used to the clothes and actually quite liked the feel of the petticoat around my legs. At times I would even feel my little cock grow hard at the feeling. That made me blush with embarrassment when I realised why, but luckily the voluminous material hid any sign of my tiny erection.
Sometime in the evening, after I had been made to help with preparing the meal, Mum decided I had had enough punishment. She took me to one side and said I could get changed back into my own clothes so long as I promised I would not be afraid of spiders again and apologise to my sister. I started to say I just could not promise as they really, really scared me. I apologised for being scared but said there was nothing I could do.
That angered Mum again and she said that if I was not going to do the manly thing then I could just as well stay as a girl. In fact she said, I should learn to be a proper girl and start to practice my make up. With that she led me to her bedroom and sat me in front of the mirror where she proceeded to make me up. It was everything, face powder, eye make, lipstick. I remember the lipstick tasting very strange indeed and in the mirror it made my lips look very different: big and red. My eyes were dark as was the fashion then and I hardly recognised myself. I felt my cheeks flush as I blushed. Unknown to Mum this was turning me on and I could feel my cock hard in the frilly panties. Her final idea to humiliate me was to get her curling tongs out and curl my hair into ringlets: I ended up looking like her idea of the ideal young teenage girl, pretty and very girlie.
'There now, you can be my daughter until you go to bed now. Do you want some dolls to play with?' I mumbled 'no' and she laughed. 'Perhaps I should call Paul to come and play then?' Paul was my best friend and found myself pleading with her not too. She just laughed and led me back downstairs. For the rest of the evening it was watching TV dressed up with her and my sister regularly making jokes about me. Finally, as it was late enough I could claim to be tired and said I was going to bed.
'Not so fast young lady' said my mother. At that she rushed upstairs and in no time was back. In her hand was one of my sisters nighties. 'You didn't think you could wear pyjamas did you?' At that she followed me upstairs and made a a point of taking my pyjamas away and laying the nighty on the bed.
I was just relieved when she left closing the door behind me. I knew what I wanted to do. I kicked off the shoes and wriggled out of the panties. I lay back on the bed and my hand reached for my cock through the petticoats and soon I was wanking away hard. I had only discovered the pleasure a few months ago but was already an expert. I felt I was near to cumming and reached for a tissue as my hand moved under the skirt and petticoat. As I did I looked at myself in the mirror, it wasn't me but a pretty girl. I stopped pulling for a second and rearranged the mirror so I could see myself laying on the bed. I organised the petticoat and skirt so that in the mirror I could not see my hand. Finally happy I watched the pretty girl and felt the most amazing orgasm build and felt myself gush into the tissue. The girl smiled back at me.
As I came down I undressed. Careful to fold everything properly and put on the nighty. It felt different again. Silky against my whole body. As I got into bed I was hard again and soon I was cumming again. In fact that night I actually came five times.
In the morning Mum obviously decided I had been punished enough and after yet another lecture finally let me wear my own clothes little knowing she had started a lifetime of fantasies for me.
From then on the idea of being made to dress as girl was a huge turn on for me. When a little older I even bought myself some girls clothes to play in, but somehow it was not right. To this day I long for another woman to MAKE me dress up but it's never happened. But that has not stopped it being the major source of my solo fantasies!