These events happened back in 1969 a few weeks before Christmas. I was 10 at the time. You can tell they had a big effect on me as I remember the date so well.
My parents were going off to my father's company 'do' as they called it. It was at a large hotel in London and as they were going to stay for the night it meant I needed to be supervised. I objected feeling I was old enough to look after myself but they were insistent. The solution they came up with was for me to stay with my Aunt Barb (short for Barbara I assume but I never did know for sure). In fact she was not really my Aunt at all, just an old school friend of my Mother's but there was this weird convention in my Mother's circle that all adults had to be called Uncle and Auntie by children ' it was not something I even really thought about: to be she had always been 'Auntie Barb'.
The night of 'do' came and I was dropped off at Auntie Barb's house as my parents left to go to the event. She lived in quite a large house compared to my parents - she had been widowed quite young and I never knew her husband, although I do remember my parents saying she had inherited quite a bit of money from the insurance and also got compensation from her husband's company which was how she was able to afford such a big place. She had one daughter a few years older than me who was away at college so we were alone in the house. I remember she looked very different from my mother who was pretty typical 60s housewife. Auntie Barb worked as a makeup artist in a big local department store and was always perfectly turned out and fashionable in a way my mother never was. I clearly recall that that evening she was in a short print mini-dress with black boots. Her hair was jet black (I now suspect it was dyed but that did not cross my mind at the time) and cut into a sharp angular bob. I only have to look at a picture of a Vidal Sissoon model of the era to be reminded of her. Needless to say she was also perfectly made up with very heavy eye mascara and eyeliner. She was not that tall but very slim ' in fact virtually the same size as me at the time.
The evening started pretty uneventfully - she made us something to eat and we spent some time in the kitchen as we ate it chatting about music. I was not actually really interested in it much, but she seemed to know a lot about it. After dinner we went into her lounge and watched some TV. In the background I was aware of her looking through a catalogue and fiddling through a box of different makeup.
'I've got to do a big demonstration in the store tomorrow.' She said as she saw me looking. 'I hope you don't mind me going through it.''
I mumbled something like 'of course not' and continued watching TV. After about another half hour she asked if I wanted to help her and I responded positively not really knowing what she wanted.
'You can be my model. I really do need to practice and your face is nice and clear - I'm sure you'll be perfect.'
I think I half started to protest but did not really get the chance.
'Come through here - I've got a little studio in the spare room.'
She led me through to another room where there was chair in front of a mirror and a table full of makeup. I was sat in the chair as she gave me a robe 'to stop messing up my shirt'. She also put a hair band over my face and pulled back my hair ' in fact my hair was a lot longer than hers: the 60s being about long hair and even at my young age I was trying to be fashionable and grow. When she was satisfied I was ready she turned the chair to face her and away from the mirror and started on her work. I don't really remember exactly what she did, but I have a vivid of recollection of how I felt. I could smell her perfume as she brushed powder on my face and I remember my face feeling hot from blushing. There was something strangely erotic about her closeness and I know my cock was solid under my trousers although at the time my knowledge of erotic feelings was very, very limited.
I think she worked on my face for about an hour - I remember the care she took in drawing the eyeliner around my eyes and the strange view as she brushed mascara on my lashes. I know the final thing she did was put on the lipstick ' she had me pucker my lips as she painted it on and I remember the taste seeming very odd. I also know that all the time she worked on me she was chatting away but I do not remember a single thing she said.
When she was finished she seemed pleased with the result.
'Not at all bad ' even if I do say so myself. Do you want to see?'
I think I nodded and she started to turn the chair round but then stopped as she was doing it.
'You know, you really are quite pretty. Would you indulge your Auntie a little more? Would you let me take some pictures? I need some for my portfolio and you really would be perfect.'
I remember blushing at being told I was pretty - an alien concept of boy of 10. She continued to talk and I got the gist that she wanted me wear something that suited the make up for the photo. She led me up to one of the rooms upstairs that I guessed was her bedroom. Once up there she took the robe and hair band off me (being careful not to disturb the make up) then started hunting in the draws and cupboards. I remember her remarking that it was lucky we were the same size. Eventually she settled on blue mini dress for me to wear. I was rather embarrassed about putting it on and she laughed and turned away as I removed my shirt and trousers and slipped it. It felt weird - sort of like a long shirt. When she turned back she laughed.
'I think taking off your shoes and socks would be better, and those underpants don't really help either!' I blushed to realise she could she my underpants with my stiff cock in them
I took off the shoes and socks as she ferreted around in some more draws and eventually pulled out a pair of frilly light blue panties. Here try these. She turned away again and I quickly slipped out of my pants and into the panties. They felt strange and soft compared to my own. That done, she said she wanted to make a few final touches before taking the pictures. She got out some heated curling tongs and did things with my hair and then finally put a pair of clip on earrings on me - they hurt a bit a first and I think I let out a little noise.
'There. Perfect. You really do make a very pretty girl. What do you think?'
She led me to a full-length mirror. I was amazed at who looked back. It did not look like a 10 year old boy, but a rather pretty teenage girl. Being the 60s my lack of breasts was actually quite fashionable and I looked not much different from many models I had seen in magazines. She had curled my hair then pinned it up on top of my head in a way that made me look older and also kept it clear of my well made up face.
I was still admiring myself in the mirror when she came back with her camera. It was large and professional looking with a flash. She had me pose in several positions around the house and in between each pose would touch up the makeup. By the end of the pictures I was really enjoying myself and vamping it up outrageously for the camera. I remember us both laughing a lot.
Eventually she was finished. She looked at the clock and exclaimed:
'God is that the time!' It was gone midnight. 'I promised your parents you would be in bed by 10. This can be our little secret can't it?'
'Sure' I replied.
'Good. Now I'd better show you your room.'
She led me to a spare room and I followed. She showed me where the washbasin was and also the nearest bathroom then finally said good night.
I realised I was still in her clothes with the makeup still on. It felt very good although I was not sure I should admit to myself how good it did feel. Reluctantly I took off the dress and panties and was about climb into my pajamas but something stopped me. I looked through the drawers in the room and luckily found what I was looking for very quickly. It was frilly baby doll nightdress. I slipped it on and lay on the bed, imagining myself posing again. My little cock was hard but I managed to hide it between my legs as I looked in the mirror. I was a sexy model just like in a magazine that had circulated around the playground. I lay on my stomach looking into the mirror making pouting expressions. As I did I rubbed my cock against the sheets and it felt good. It was not long before it was so hard and uncomfortable I had to role over. Still wanting it to feel good I took it in my hand and rubbed it. It was not the first time I had 'played with it' as I called it but it was the first time it was very special. My mind was filled with erotic images of me modeling - modeling as a sexy girl at that and soon I think I came for the first time. There was no real ejaculation but there was some thin white fluid oozing out and as I came my whole body shook. Afterwards I felt very content and quickly fell asleep.
The next day I was woken up by Auntie Barb while still wearing the nightdress I had found. She said nothing about it, but suggested she help me take off the makeup from the night before. She did it very professionally and by the time I had showered and washed my hair there was nothing to show from the night before. Over breakfast she said nothing about the previous night and the only hint she made was when my parents came to pick me up and she said 'Thanks again, you were a big help last night.'
Nothing like this ever happened again, but it has given me masturbatory fantasies ever since. Although straight and now married with kids, every time I masturbate in my mind I am a sexy model. Sometimes I grow boobs, sometimes I even have a pussy and get fucked, but always I am in front of a camera.
There was one short postscript to this story. A few weeks later Auntie Barb dropped round when I was alone in the house. She had a copy of the photos for me. I keep them to this day as a memento to a very, very special night for me.