Aunty Put Me In Dresses - Panties - A Photo Story

I was the youngest of five boys so you can imagine the chaos in my house with all that testosterone and boisterous energy in the air. But I wasn’t like my brothers – I could feel this from a very early age. I used to enjoy escaping to the serene environment of my maiden aunt’s place a number of streets away. I started doing this from a very early age and I guess I adopted her as my other-mother – my real mother was well over raising children by the time I came along. My aunt was a seamstress and she used to get me to model her garments as she applied the finishing touches. Most of the dresses were sizes too large and I would have to stand on the low coffee table but often she would have an order for a debutant gown or even a teenage party dress or skirt.
I didn’t mind being the mannequin for aunty because I was always rewarded with lolly-water and cake – or even chocolate biscuits – these things were never available at my house and I had a sweet tooth.
But aunty was as strict as she was generous and she would make me to help her with the housework. For this she would make me wear what she called a “pinny” which was just like an apron-dress that fitted over the head with a back and front that tied at the sides. She would also insist that I take off my outer boys clothing so that they wouldn’t get dirty as we cleaned. I was embarrassed at first as my underwear could be seen at the sides and when I bent over or reached up. But as there was only she and me in the house I didn’t complain. I would work under her strict direction but I didn’t mind, as I knew there would be treats waiting.
But the real treat was simply being in her company, sitting at the kitchen table chatting – and I didn’t realise it at the time but our conversations were very “girlie.” She would ask my opinion on fabrics and clothes as we went through sewing books and catalogues.
In one of the sewing books was a pattern for a pleated skirt and I must have shown particular interest in this. I think I was intrigued as to how the pleats were made and that it must be very laborious. Aunt saw this as a challenge, I think, for the next week she had made a pleated skirt in my size.
I loved wearing that skirt from the moment I tried it on and Aunty recognised my joy for she suggested I keep it on as we did the housework “just to see if the pleats would last.”

From that day on, when I arrived at Aunt Clara’s house I would slip out of my boy’s clothes into a dress for she then proceeded to make a number of dresses in my size.
One of the dresses was a short sundress and was tight around the waist. Unfortunately the thickness and bulkiness of my boy’s undies showed through the fabric and Aunty said that this would never do. And so a pair of thin nylon girl’s panties was produced and I wore these from then on under my dresses.
Of course my aunt had told my mother about my predilections and I think she was a little envious of my aunt – after all she had 4 other boys to be boys and she had always wanted a daughter. I was to learn later my mother had wished that I had been her daughter and helped her with the housework.
One Saturday afternoon as I was busy doing the housework at my aunt’s, the doorbell rang and to my embarrassment aunty invited in a number of her friends for afternoon tea. I immediately hid in the laundry but aunty found me and insisted I stop being so silly and that if I wanted to continue to visit her I had better “come out this instant and meet the ladies,” which reluctantly I did. However, to my surprise the ladies were not shocked at seeing a boy dressed as a girl. This may have been due to the way I was introduced. Aunt had made out that she wanted the ladies to see her latest girl’s dress and that I was kind enough to model it. “My, but you do make for a sweet little girl don’t you,” one had said and some strange excitement raced through my whole body.
Aunt Clara asked me to make the tea and serve it to the ladies, which I did. I was greatly embarrassed at being her “maid.” One of them even lifted my skirt and made a comment about the prettiness of my panties which sent my face bright red.
“Did you make the panties as well, Clara,” one asked and after aunty had said yes, of course all the ladies wanted to see and I had to stand with my skirt raised as they all viewed my nether region from all sides. Of course the thin nylon material offered little protection for my budding manhood and I was embarrassed that they were able to clearly see all the details which was giving them some amusement. I remember hearing one of them whisper to her friend behind her hand, “he’s very small down there isn’t he.” This comment has always remain with me – because I was very small down there- and is probably one of the reasons I chose not to compete with my brothers and other boys – instead choosing a different path.
Aunt Clara was asked about other dresses she had made for girls and I then had to model these, slipping into the bedroom to change and then returning and performing as if I were a catwalk model. Under their direction, I would swish the skirts so that they flew high around my body. I was told to lift the skirts at the front and back so the ladies could view the different styles of panties. My collection of panties, courtesy of aunty, ranged from full white cotton schoolgirl bloomers that went from waist to thigh to skimpy thongs that barely covered what they should. There were panties clearly designed for a little girl with pretty motifs of flowers and angels and ruffles over the bottom and then there were naughty silky tight panties for the teenager
By now I was staying overnight with Aunt Clara, and she had made me nighties and baby-doll pyjamas – which were the rage back then. I loved climbing into that large soft bed with its pink sheets in my silky nightie and would fall asleep contented. Quite different to the room at home which I shared with two other boys.
As time passed, Aunt Clara and I became more game. My hair had grown longer, as was the vogue in the late 60’s and Clara would make it feminine, often with small pig-tails on either side at the top or she would simply add a hair band. Then some light make-up and we would venture to the shopping center where we would go through the dress shops. This was always followed by a treat – lunch in a restaurant where I could order what ever I liked. This particular shopping centre was on the other side of town and so there was little chance that I’d run into school friends. Even so I kept a watch out.
At first I was very self-conscious and was sure that everyone could tell I was a boy dressed as a girl – and some did give me double glances and I would just look down in embarrassment.
But Clara was teaching me how to walk, talk and behave like a girl. I remember one instance: we were sitting on some high stools at a bench in the food hall having a milkshake. The floor in front of us was lower and a group of teenage boys were sitting at a table. I didn’t pay them any mind but eventually Aunt Clara whispered in my ear: “Are you sure your knees are together as any good girl would have them?” To my horror I suddenly realised that I had been sitting as any boy would with my legs stretched wide apart and of course the boys were all enjoying the view of my panties and were giggling and whispering to each other. Quickly I bought my knees together and heard a muffle groan from the young voyeurs. But in another way I was stimulated by the idea that I could excite these boys simply with my body and furtive glimpses of my private region – somehow it was giving authenticity to who I was pretending to be.

If you are interested, go to my photos to see photos that compliment this story. You will see in some I look very apprehensive – yet now I realise I was loving it.
gaylord13 gaylord13
16 Responses Apr 6, 2012

Great read

My mom dressed me as a girl when I was 6. I didn't like it at first but when everyone said I was so cute I wanted to dress like that every day. My mom wouldn't let me so every Halloween I would try to be any costume with a dress. You were so lucky

a lovely story and makes me feel quite envious . as a boy I used to borrow my sister's pleated skirt and navy blue knickers (without her knowledge ) and try them on loved the feeling of freedom I could only do this rarely as we lived in a very small house and was quite crowded . I do wear a kilt but it's not quite the same as the lightweight skirt

That sounds awesome I liked it (I'm a guy)

I hope you will also read my stories as it was heaven for me when my mom invited some of her neighbor lady friends in to meet the new "me" after she agreed to help me dress & date boys. You were so lucky to have such an inclusive Auntie.

How old were u!?!

Very sweet story.
Anxious to read more, or, hear a podcast.

I am jealous of you. I lived in a home here sex was dirty so I felt bad when I saw my mom in a bra and a half slip. from that day on I would look thru the hamper in the bathroom to find what goodies I could put on even f only for a few minutes it felt so good. I feared getting any ***** on them so I would use the half slip to pull up over my privates and it made me ********* without getting any on it. I felt safe that way it has led me to a lifetime of denial that I am just now trying to release and be open about . You were so lucky to have an aunt like her.

So u were sexually attracted to ur mom?!

Would like to see the photos that accompany this story. Can you add me to your circle?

Room on the broom for one more? ;-)

A fascinating story. I can remember as a young boy trying on my mum's panties becuase I liked the feel of them. But stopped, recently however 40 years on I have started wearing my wife's, I have even wore them to work. Not a good idea because it makes me feel a little horny.

I love your story.. Wish. all could be so lucky!!!!

brand new and don't know how to use site?

Your Aunt took good care of you growing up. But she also put you to work too.

This is a wonderful collection of real-life experiences, that you shared with your aunt, her friends and your family, I would have changed places with you in a second, the most important thing to me, is that this is not something that was forced on you, every little boy has curiosities of those magical little creatures called girls, everything about them is better, they are nicer, they dress prettier and they always seem to smell better, you were allowed to share both worlds, I thoroughly enjoy the details and emotions, as you develop your characters, I really would love to see more real childhood photos, maybe even younger, thank you for sharing your life, loving and caring,<br />

Thank you for your comment, I'm glad you enjoy my stories. Its funny but I think as I get older, i seem to remember more details

A great story and your Aunt was good to you.