I would like to tell you about something that happened to me when I was a boy of 14 years old. Firstly I was a slim "pretty" boy of average height, small boned and with quite feminine features. For as long as I can remember I liked to play dress-up with dolls and put on girl's clothes. Since puberty, this had taken on a whole new excitement.
It was about this time that a very exciting event occurred. My parents and sisters were going to Queensland for a conference but I had to stay with my auntie to finish an exam at school. My Auntie and two cousins were minding a small farm near the quiet farming village of Jamboroo.
My auntie Joan was an attractive 35-year-old who was living in Sydney. My cousins Sue and Anne were quite attractive and 17 and 14 respectively. They were all very pretty and feminine in their manner and dress. The farm, being about three hours from Sydney, ten minutes from the village and one hour from the town, was fairly isolated and the weather was cooling off so not many people would be visiting.
Auntie was apparently subconsciously jealous of me being the only boy in our families and this I guess was the driving force in what was about to happen.
My family left early on Monday morning and auntie picked me up after school. Auntie had to make a quick trip to town to drop off some clothes she was having altered and we stayed around the house. On her return, she decided we should take some old paint cans to the shed. She tripped slightly and one of the cans she was carrying spilt all over me.
The paint was only on my clothes but they were ruined. I washed and went to the bedroom to find a very pretty green dress lay on the bed. There was also a lace camisole and matching panties.
I called to my auntie to ask where my clothes were and she said that my bag must have been left in my family's car by accident and that they had also left their bag with my cousin's jeans at home as well. "You will have to wear something for the next two weeks and that is all there is," said auntie. I put up some protests and went to my room.
While I knew I would enjoy wearing the pretty clothes, being a boy I knew I had to pretend that I would not like it. A few minutes later Sue (with whom I was quite close) came in and said that while she knew I would not like to wear the clothes it was the only thing to do, and she and Anne would not laugh at me or anything. Anne came in then and promised not to laugh or tell anyone. She said I should put the clothes on, as there was no one else around anyway. They both promised again not to tell anyone and then left me alone.
I could not believe what was happening, of course I would love to dress in the pretty clothes and they were not going to mind at all let alone laugh at me. I had a perfect excuse supplied to me as I saw it.
I put on the lace panties and camisole, and then I put on the green dress. There was also a pair of lace top white socks and a pair of black buckle up shoes. I looked at myself in the mirror and having missed the last couple of haircuts I looked pretty good. I was feeling very excited and was glad that the dress had a full skirt and petticoat, which would cover signs of my excitement.
The moment had come for me to leave the room. My aunt and cousins were busy in the kitchen getting dinner ready and did not take too much notice of me. My aunt told me that that was being much more sensible. Sue told me I looked fine and Anne agreed. Then they all went on with what they were doing.
My aunt asked me to set the table. We had dinner and made small talk about nothing in particular. After dinner my aunt asked me to come over so she could have a look at me. She told me that I looked very good. She trimmed my hair and combed it into a much more feminine style.
With my new hairstyle I looked very feminine and I could easily be the younger sister of Sue. On our way to bed aunt gave me a nightie to wear and some cream to rub on in the morning before I had my shower to tidy up any unwanted hair I had.
In the morning I put on the cream, washed and put on the clothes I was wearing the day before. Sue came to my room and helped me with my hair and put the slightest amount of natural colour makeup. Looking in the mirror I could see this very pretty girl looking back at me and I started to get very excited again.
From my previous experience putting on girl's clothes I had a good idea how to act and was adapting quickly. I heard Auntie Joan calling us to breakfast so off I went, more relaxed than the previous day and feeling very feminine.
My auntie told me that I looked very pretty and totally convincing as a girl. We decided that I should have a girl's name in case someone overheard us. Sue suggested Julie and I agreed that I liked that. We finished breakfast, then my auntie put out some more clothes for me so I would have a change. She suggested we go for a walk.
I was not sure if I was ready to go outside but everyone convinced me that I would be fine. I would certainly not stand out at a distance anyway with everyone dressed in the full-skirted dresses that were fashionable at the time. It was wonderful walking across the paddocks with the skirt of my dress brushing against me and the light breeze blowing our skirts around. A larger gust of wind blew all our skirts up revealing petticoats and panties. How exciting it was. We were all enjoying this lovely day and just being so feminine.
We had walked much further along the creek than we had thought. We were now on the next property. Much to my shock, we ran into someone else - a 15-year-old boy called Luke. He knew my cousins and Aunt and I was introduced to him as Julie. I was frightened he would know I was a boy but was still very excited that someone else could see me dressed up.
To my surprise and enjoyment, he accepted me as a girl and seemed quite interested in me. We all sat on the riverbank and talked. Luke had positioned himself on the bank below us where if we wished he could get a good view under our skirts. We all took pleasure in giving him what appeared to be accidental but were actually quite deliberate glimpses of our panties and up to our skirts. Luke was obviously getting very excited although he did not realize we had noticed.
We were enjoying teasing Luke but it was getting late, so we said our goodbyes and promised to meet tomorrow. We walked back up the bank and Luke watched us until we went into the trees. Sue made an excuse about forgetting something at the river so she asked me to return with her to get it.
We hid in the trees and could see that Luke was still at the edge of the river. He was looking around and obviously thought he was alone. He had pulled down his jeans and underwear and was certainly enjoying himself. He was very excited, and Sue and I were getting excited about watching him. Sue slid her hand under her skirt. I could not see much but she was enjoying herself and was not worrying about me watching her. Sue straightened herself up and said we had better go. I was feeling very randy.
We made it back to the house had dinner and went to bed. I took the opportunity of being alone in bed to relieve the pressure built up due to today's fun. The silky nightie on my body did the trick.
In the morning I showered and put on the padded lacy bra and panties, white petticoat and the pale ye1low dress. The dress was soft and the petticoat made the skirt full swish as I walked. Auntie Joan complemented me on how I looked. I was getting the idea that she was enjoying me being dressed and acting like a girl. I was enjoying it as I well - for the first time I was feeling so complete and full.
Sue, Anne and I sat outside under the trees and talked about clothes, and boys, and making out, and about seeing Luke pulling himself off.
While I still considered myself a boy, the way I was dressed and acting made this all feel so natural. Sue told us how she would sit in the front seat of the bus because she knew that the boys behind could see up under the skirt of her tunic in the mirror. She enjoyed the idea of all the boys getting hard looking at her. She also liked to bend over a bit more than she had to, teasing the boys.
Auntie and my cousins decided to go to town but despite the protests, I decided I was not ready yet to let other people see me. After they left I went for a walk and ran into Luke. At first, I was a bit unsure but after I realized he was convinced that I was a girl I decided to have some fun.
It was still a bit gusty so my skirt was blown up revealing my petticoat and panties. I could see that I had his attention so I forged on. I sat on the bank and knew he was able to see up my skirt. Then we went for a walk. He was holding my hand and helping me down over some rocks. Taking some advice from Sue I was able to make sure Luke could get lots of good views under my skirt, and it was obvious that it was all having the desired effect. Luke was getting turned on - and strangely enough so was I.
Over the next rock, I gently slid my body down against Luke. He held me for a moment and then I put my lips against his and kissed him. He was very shy and surprised but he enjoyed it. We sat back on the grass and kissed again. His shyness gave in to his passion and he awkwardly slid his hand under my skirt and around my bottom. He slid his hand into the back of my panties and I felt very aroused but I had to stop him before I was found out. I grabbed his hand and said that it was that time of the month. He nervously pulled away. So I reassured him I could still kiss and make him feel nice. Twenty minutes passed as we talked and cuddled. I had to get back so we repaired ourselves, kissed and parted.
On the way back up the hill, I ran into Sue in the bushes she had watched the whole thing. She held my hand and we kissed on our ruby lips. Laying on the ground our legs entwined and hands groping under our skirts. She then removed my panties and threw up my skirt and petticoats. How nice it was as I felt her touch me. It had all been too much. We smoothed our skirts and returned to the house for dinner with our secrets.
The next day we seemed to just continue as though nothing had happened. I dressed in a soft white cotton blouse a full navy blue skirt and white petticoat. I did my hair and makeup. I was getting well practised with my hair and makeup and was looking better. The makeup was very natural and not too much for a girl my age.
At breakfast, auntie announced that we would go to the village for some groceries. She added that she was sorry there were no clothing shops in what was only a village. I was glad of that but I did not let on. My auntie commented that I seem to be happy to wear girls clothes now and I said that they were not too bad. I tried not to seem too excited.
I was not sure about going to town but knew I would not be able to get out of it this time. We all headed for the town in the car dressed in our pretty dresses and skirts. I was filled with excitement and fear at some one else seeing me. My cousins told me that I would have no problems passing for a girl and not to worry.
In town, we walked from shop to shop. I was being introduced as Julie and no one seemed to question my being a girl. How exciting it was. In fact, most people thought I was the most attractive. What fun. Sue and I spent the morning flirting with the boys and when the opportunity presented itself bending over counters causing our skirts to be pulled up and giving the boys a good look at our panties. It is amazing what fun it was teasing the men and boys.
Back at the farm, we had lunch and then went for a walk. It was a beautiful sunny day walking through the paddocks. There was a gentle breeze blowing with a few gusts that would blow up our skirts and petticoats. The breeze was wonderful swirling under our skirts. I wondered if the others were enjoying everything as much as I was.
It was quite late when we returned from our walk so we had an early dinner and went to bed.
The next morning was a bit chilly, so after putting on my lacy bra panties and camisole I put on a top and a warm full red skirt. Then I put on a cream jumper that came to my waist. At breakfast that morning I saw the others had dressed much the same - I was happy to see I was getting the hang of being a girl because I really enjoyed it.
After breakfast, my auntie had to visit someone so she dropped us at the beach to play. It was far too cold to swim today but we had great fun playing around in the bush in the sand dunes. On the way, we grabbed at each other's boobs and flicked each other's skirts up much to the excitement of some teenage boys on the beach.
How very exciting it all was. We were playing around in the rocks on the beach and having a great time feeling so feminine. We walked along hugging each other and flicking up our skirts. It was a great day. After a couple of hours of playing around, we saw someone, it was Luke.
Luke came over and we talked for awhile and flirted with him flipping up our skirts accidentally and making sure he was getting turned on. Sue enjoyed flirting and I was enjoying it too. Poor Luke had to put up with our teasing for the next hour. Then again maybe he was enjoying it too. I was certainly enjoying being a girl.
What a holiday this turned out to be and we still had three weeks to go...
