The Backdoor View – 1
by Josephine Gonsalves
Early memories and events
It started way back in 1967……a long time ago…I was 10 years old at that time, but I can remember it like yesterday. I was an unobserved witness to a cross dressing incident that effected my thinking….and many other aspects of my life.
It was a September afternoon. I was at home and not at school as my class had gone for a picnic, but I had not gone as my father had died only the week before. I was bored and so took my catapult and was trying to shoot some pigeons or parrots that were always to be found in the trees near Aunty Margaret's cottage. I had fired a few shots when the rubber band of my catapult gave way so I just squatted down besides the water tank, on the top of the outdoor toilet. In our part of town the toilets were built a little distance from the homes. It was an unusually quiet afternoon, no infants crying, no radio, music or car sounds so I stayed quietly in my perch from where I could see the back verandahs of all the adjacent cottages. Suddenly I saw movement from the back of one of the cottage. I popped my head to peek and saw that Aunty Margaret was signaling to Aunty Rosy in the next cottage, with her hands and in a hushed voice. Aunty Rosy was wearing a saree, which meant that she was going out. I saw her wave back to Aunty Margaret and go inside her house. A little later she stepped out holding a large traveling bag. She closed her back door quietly and quickly and went across to Aunty Margaret's back door. I was surprised to see Aunty Margaret, as she was working for a well known pharmaceutical company and it was a week day. In a little while I saw Aunty Margaret, who was in a cotton nighty, go to the end of her porch and wave out to someone down the lane. The person came into view and I saw it was Arthur. Arthur was wearing a shirt and cut off shorts. He looked like he had just had a shower. He looked around and seeing no about, proceeded to Aunty Margaret's house. In the meanwhile Aunty Rosy and Margaret had already gone inside. Arthur reached the back door of Aunty Margaret's house and was let in quietly.
My curiosity got the better of me. I looked around and seeing no one about, climbed the tiled roof of Aunty Margaret's house, which had smoke tiles (tiles with vent opening for ventilation purpose) and large glass sheets in the middle of all the rooms for letting in natural light. Joe my friend and next door neighbor, knew about these glass sheets. He and I had many times climbed the roofs of these cottages, in the dark and watched our female neighbors undress and dress in their bedrooms. We could see thru the glass and hear thru the openings in the smoke tiles. The experience was thrilling but we were afraid of the consequences if we were caught peeking.
Let me introduce the people involved…..( In our place, we called all our neighbors Aunty or uncle, if they are older than us or in their 30's and above, out of respect.). Aunty Margaret was a 40 years old, buxom spinster who worked in a big pharmaceutical firm. She dressed in tight skirts and blouses which highlighted her big boobs and shapely behind. She was rarely seen without make up. She had been widowed in her first year of marriage when her sailor husband had died in a shipping accident. In spite of many admirers she had stayed unmarried. She was not given into sorrow and was very kindhearted and generous. She often sponsored our neighbor hood lotto evenings and was friendly with all the youngsters. We often did her errands, for which she tipped us well. Overall she was a good natured woman. Aunty Rosy was a little younger than Aunty Margaret. She was married and had two young daughters. Her husband was an auto mechanic, who worked long hours. She wore skirts and blouse when at home but wore sarees when she went to the market or for outings. She looked very good in sarees. She was also well endowed with a good pair of boobs and a well proportioned behind. She and Aunty Margaret got on well and went shopping and did things together.
Arthur was a twenty something young man. He stayed alone in a small one room apartment in the adjacent chawl # 2. He repaired radios and household appliances. He also did household electrical wiring and repairs and so everyone in the neighbor hood knew him. The young girls liked him for his good looks and naughty comments, jokes and happy attitude. He also played the guitar and sang making him popular at birthdays or other community functions.
Now onto my story…..I crouched quietly on top of Aunty Margaret's glass and watched the going on inside. Arthur was not in my vision, but I was in time to hear Aunty Margaret tell Aunty Rosy, how she had dressed Arthur in her skirt and blouse last month. Aunty Rosy asked how it had happened and Aunty Margaret said that it was not planned. Arthur's work pants seam had given way while climbing the step ladder, as he was rewiring Aunty Margaret's bedroom. Aunty Margaret had jokingly offered him her skirt. He was embarrassed at first, but she continued joking and as they talked one thing led to another, till she had coaxed him to try her clothes and he had ended wearing her bra, skirt and blouse. What started as fun got very exciting for both Aunty Margaret and Arthur. It progressed to touching and light petting and finally to kissing and caressing. They had stopped at that, but the effect of wearing her clothes had Arthur sexually stimulated and he had requested Aunty Margaret to help him dress more often. She too had liked it and so she had continued dressing him in her clothes secretly. Aunty Margaret had a few wigs and concert costumes that our local amateur "Goan theatr" group had kept with her. She had used these and her own clothes to dress Arthur. Arthur had looked quite convincing as a woman, so now he wanted to experience going out and so she had planned to take him for a movie dressed as a woman. Unfortunately he had hairy legs, which he did not want to shave. It would be noticed by the others, as he often wore cut of shorts. Aunty Margaret realized that with a little make up and right clothes, to cover his legs, Arthur could be transformed into a good looking woman. Aunty Margaret suggested that he would have to wear a saree for this purpose and she would click some photographs. Arthur said that he would be thrilled to wear a saree. Aunty Margaret said she too would wear one for the photo session and that's how she decided to ask Aunty Rosy to dress them both.
I watched as Aunty Rosy dressed both Aunty Margaret and Arthur in sarees that she had brought with her, in the traveling bag. Aunty Rosy asked Arthur to strip down to his underwear and wear a bra, a saree petticoat and blouse. Aunty Rosy and Margaret debated about the size of his breasts and what to use as padding, but Arthur was by now familiar with Aunty Margaret's underwear and soon he was clad in Aunty Rosy's petticoat and a nice fitting blouse under which he wore Aunty Margaret's well filled out bra. By now even Aunty Rosy was enjoying herself. Every now and then she caressed Arthur's behind and new boobs, and joked saying she did not know he was a "sissy", which I could not understand at that time. In the meanwhile Aunty Margaret also got dressed in another of Aunty Rosy's saree petticoat and blouse. What a sight to see her almost naked body. My own excitement was mounting. Aunty Rosy now shifted her attention to Margaret and helped her with her bra and petticoat. It was quite interesting watching Aunty Rosy touch Margaret in intimate places as she helped her dress. Aunty Margaret seemed not to mind and looked very happy to be touched liked that. It was quite a pretty picture, seeing a young boy and a buxom woman in semi attire, being dressed by a woman who was enjoying dressing and touching them all over. Aunty Margaret then had Arthur sit while she did up his face. I watched trying to take it all as she powdered his face, applied lipstick to his lips and eyeliner to his eyes lashes and darkened his eyebrows. Arthur sat there docile and just did whatever he was told to do, like an obedient girl. When finally the wig and jewelry were fixed on him, I could not recognize him. He looked very attractive. In fact he looked more attractive than Aunty Rosy or Aunty Margaret. He looked prettier than most of the women and girls in our neighborhood. Aunty Rosy then draped the saree on Arthur while Aunty Margaret helped him into a pair of heeled slippers. In a little while Arthur was transformed into a very attractive young woman. Aunty Rosy showed him how to adjust the saree and how to lift the pleats and walk. I was so engrossed in Arthur's transformation, that I forgot everything around me. I also noticed that I was feeling a new sensation in my childish penis. The feeling was different from any I had experienced before.
Aunty Rosy then helped Aunty Margaret drape her saree. I could tell that Aunty Margaret was used to wearing a saree. Aunty Rosy had to drape it around her just like she did it for Arthur. Now it was Aunty Margaret's turn to stand docile as aunty Rosy dressed her. There was a lot of times I saw Aunty Rosy's hands pass lingeringly across Aunty Margaret's breasts, buttocks and waist. I did not understand it at that time, but I guessed that it was sensuous, as they were silent and the motions were looked very slow and deliberate. I watched quietly realizing that the pictures of Aunty Rosy dressing Arthur and Aunty Margaret were being stamped on my mind. It was the first time I realized there was a lot more to just the saree. The under things were also attractive. Besides there were the make up items like lipstick, eyeliner, jewelry etc. All these required practice and some skill. When they were ready, I heard Aunty Margaret tell Aunty Rosy that she had made an appointment at the photo studio on the main street.
Aunty Margaret went to the door. She cracked it open and checked that all was quiet outside. They guided Arthur between them outside and started walking towards the Studio .It was sunny outside so they opened up a parasol and held it so that Arthur was shielded from the sun. When I look back on this scene it reminds me of scenes where a mother or mother in law prepares her "bahu" for an outing. The street was quiet and empty. I quickly scampered down from my hiding and took a short cut, by climbing the walls of the compounds, so that I was at the studio, before they reached it. I saw them approaching, three woman dressed in Sunday wear sarees and well made up faces. Two middle aged Aunties and one young woman. I pretended not to notice them as they approached me. Then when they were near I suddenly turned towards them and greeted both Aunty Margaret and Aunty Rosy by their names, but stopped at Arthur. I looked at Arthur and then wished him "good day aunty" too. Aunty Margaret and Rosy greeted me but continued walking. The "other Aunty" just nodded. I followed closely as they tried to tell me not to follow, but I was suddenly excited and curious and wanted to know what they had planned for Arthur. I followed them and sat quietly in one corner of the studio.
The photographer was reading a newspaper but quickly got his act together and welcomed them. Soon the studio was lit up and last minute touching up was made. I watched as he helped them strike different poses. Aunty Margaret told the photographer to focus mainly on Arthur. So he clicked Arthur in many different poses, sitting, standing, side profile, with pallu covering his head, with pallu around his shoulders, and even with the pallu down, exposing his blouse. Then he clicked Arthur along with Aunty Margaret in different poses. Aunty Margaret asked for a few pictures of Arthur sitting her lap. These pictures really sent a little thrill down my body. It was so different from "the natural" to see a male being seated on a woman's lap. The photographer did not know, he was under the impression that they were all women. Then aunty Rosy joined them in a few photos. The best pose was of Aunty Rosy sitting in a chair with Arthur and Aunty Margaret sitting on both sides of her on the arm rests. Finally Aunty Rosy asked for a picture with Aunty Margaret sitting in her lap. She held Aunty Margaret around her waist and back, while Aunty Margaret had her hands around her neck. They looked at each other and not the camera for this picture. All thru the photo session there was a lot of touching and soft caressing, which I found very exciting, yet disturbing. When the photo session was complete they thanked the photographer and proceeded to the new Udipi hotel. I followed them and sat in the seat next to Aunty Rosy. They now noticed me and ordered a plate of hot wadas. I pretended that I did not recognize Arthur and called him aunty all along. Aunty Margaret then whispered in my ears that the "Aunty" was Arthur and they were practicing for the next month's "theatr". We finished off our refreshments and we walked to the bus stop and waited for the bus. The bus arrived. Aunty Margaret and Arthur got onto the bus, while Aunty Rosy and I started for home.
On the way Aunty Rosy explained how Arthur was going to perform a solo song as a woman. I asked her why he had to perform as a woman when we had so many young women who could sing. She said that many of the young women were afraid of singing in public, due to stage fright. Besides it was a novelty for a man to perform as a woman. I nodded and saw the look of content on her face, satisfied that she had answered my queries. We reached home and I went off to play as usual with my friends who had returned from school.
The image of Arthur in a saree, however stayed in my mind. The more I thought about it the more intrigued I felt. I suddenly had a need to go to the bathroom. There I discovered my penis had become stiff and I was feeling a little funny. I waited that evening to see when aunty Margaret and Arthur would return. But it soon got dark and I was called home by my mother. I wondered what Aunty Margaret and Arthur were up to. Many years later and after reading articles on crossdressing, I had a smudged impression.
True to Aunty Rosy words, Arthur performed a solo song, which he sang in soft falsetto. He wore a red saree and was all dolled up. Many of the people watching could not believe that it was Arthur and they called out for an encore after his performance. Arthur obliged and the audience loved him. After the show I went up to him and told him that he was wonderful. I also told him that he looked better than most of the women present there. This made him smile. A lot of other people came to him and congratulated him. Finally, Aunty Margaret and Aunty Rosy came up to him. Someone had a camera and they asked them to pose. This time there was no secret and they posed for the pictures, Arthur the 'star with her admirers".
I got to see Arthur perform a few more times and each time I was more fascinated and a desire to perform as a woman was building in me. I had sung in the school talent contest and church choir. I had a nice voice, but there were better boy singers than me and I was relegated to the back ups and choir. I now saw a chance where by I could be in the limelight. If I could dress as a girl and perform well there were a lot of opportunities for me. I also started fantasizing about how nice it would be if Aunt Margaret and Rosy would dress me in their clothes.
That incident clearly stayed in my mind. I slowly started enjoying movies where the men dressed in women's clothes, especially sarees. I also started reading stories with cross dressing content. My desire to dress in female clothes was now increasing. I found I enjoyed fantasizing being dressed as a woman. I secretly wore articles belonging to my mother, while I was alone. My crossdressing started out wearing bras, slips and petticoats. My chance to wear female clothes in public came soon as I was selected to play a girl in the class play. However I did not get an opportunity to dress in my favorite female fantasy dress ……the saree, till much later.
A boy amoung the girls
I had witnessed Arthur being dressed in a saree and transformed into a woman. The incident clearly stayed in my mind. The scenes of Aunty Rosy touching Aunty Margaret and Arthur in an intimate way also stayed on my mind. So whenever I saw Arthur I felt a funny sensation. Here was this handsome guy, who secretly dressed up as a woman and enjoyed it. How he reacted to Aunty Margaret and Aunty Rosy in ordinary everyday life, did not suggest any special friendship between them. He seemed normal and no one besides me knew about his and Aunty Margaret's secret liaisons and Aunt Rosie's involvement. It was a big wonder to me how a popular young man, willingly dressed as a woman and went out secretly with an older woman. I wondered what pleasure he got from wearing female clothes and being treated like a 'girlfriend'. I also sensed that such behavior was not looked upon kindly by society. If it was so then why were Aunty Rosy and Aunty Margaret dressing Arthur in secret. My curiosity got the better of me and fanned by comics and comedy movies of Laurel and Hardy, Indian comedians like Mehmood etc, who dressed as woman for laughs, I decided to find out more about such behavior. At that time in the 60's, there was very little info or writings on such behavior, besides these so I guessed that dressing in the opposite gender's clothes was more for "stage' and movies, to create comic scenes. Yet, whenever I read or saw such scenes I was thrilled and imagined myself as the one dressing in female clothes. My imagination took over and I started fantasizing often about wearing women's clothing. I lived in a two room tenement, which was part of a chawl #1 (two storied building divided into ten of twelve tenements).This was at one end of the street and the chawl # 2 was at the other end of the street. In between were the local 'better income"people cottages. These cottages had front and back porches, backyards at the end of which were the outhouse or toilets and large trees. In the backyards were clotheslines for drying out the washed clothes. The backyards had no walls, just stone markers, so the women could pass from one yard to the other with climbing or opening gates etc. I used to pass thru the yards and look at the female clothes like dresses, skirts etc. I imagined how I would look in them and if they would fit me. Sometimes the urge was there to touch or try out some of the clothing, but I did not want anyone to see me doing so. I knew that I would have a lot of explaining to do, especially if I got caught wearing female clothes without a proper reason. In time I became a little bold and started touching female clothing that were on the clotheslines. Every time I touched a piece of female clothing I got very thrilled and excited. Often if the occasion permitted I held them against my body feeling the excitement.
I had to wait a few years before I was to experience wearing female clothes. I was fifteen at that time. My face was very androgynous, as I was fair and had no facial hair yet. I was small built, short and slim and looked like a boy of twelve or thirteen. That year my family was unable to go to Goa, my parent's native place for our summer vacation. Most of the other families in our chawl # 1, had gone on their summer vacations, to their native places. Instead I joined the community/parish summer holiday club. At the club one could play indoor games, read comics or story books, play volleyball or hockey if one was inclined to. The timings were from 9 am to 12 noon and from 4.30 pm to 7 pm, every weekday. Every Thursday afternoon a western (cowboy) or Cartoon movies was screened in the school auditorium for the club members. I had just finished my SSC or high school final year, and was awaiting my results. In the meantime I was going to the local garage, every morning, so that I got familiar with mechanical work. I only attended the club in the afternoons, after 4 p.m. After the first week of attending the club, I became familiar with two girls, Lourdes and Julie, who were my neighbors and the same age as me. I had known them from when we were children but now it was different as they had changed so much.
Lourdes, who lived in chawl # 2, had grown tall and stood nearly 5 feet 10 inches, in her bare feet. Now she had a slim, boyish and athletic body. Her best feature was her long and shapely legs. Her hair was shoulder length and straight. Her facial features were oriental and flat. She had smooth dark skin with none of the blemishes, like acne or pimples that teenage girls suffered. When not in jogging pants and T shirt she wore home stitched knee length printed terry cotton dresses (mostly to church). She looked much older than her age and joined the boys in playing volleyball and basketball. Since she was taller than most boys our age, she was called "tower". She was popular with the boys, as she took part in all their impromptu fun games. Julie the other girl, lived in one of the cottages, was the opposite of Lourdes. She too had grown and was around 5 feet 2 inches tall. She had fair skin and a pretty face, which was highlighted with clever use of "kajal" or eyeliner and light lipstick. Her hair was long and dark auburn in color. She had a nice figure with well developed boobs and buns, making her a 'hit' with the boys at the club. She wore short skirts and tight blouses that showed off her big boobs and round behind. She too joined the boys in playing games, but she was not as athletic as Lourdes. The boys enjoyed playing with her and touching her intentionally. The two of them were always seen together. They had bicycles and rode to and from the club. Lourdes had a full sized boy's bicycle, whereas Julie had a new girl's bicycle. However on most of the days Lourdes gave Julie a lift on her cycle. Julie sat sideways on the crossbar of Lourdes' cycle making it look like Lourdes was a boy giving his girlfriend a ride. This prompted many of the boys to tease them saying that they were a 'lez' couple. I had seen a few pictures in adult magazine secretly and knew what it meant.
They seemed very friendly and nice and we slowly became good friends. Then I started accompanying them to and from the club. At first Julie used to give me her cycle and Lourdes used to give her a ride, but Julie had to go for stitching classes sometimes and so Lourdes started giving me a ride, whenever Julie was not with us. The first time she offered me a ride, I was reluctant and finally hopped on to the carrier at the back. Lourdes however said that it was difficult to control the cycle while turning and convinced me to sit astride the bar, in front. Sitting in front, I felt like a girl being taken by a boy for a ride. At first I was shy that the other boys would tease me. Lourdes guessed and so I sat behind whenever we were near the summer club. Once we were a little way off, she stopped and I changed position and I sat up front. Sitting in this position I was between Lourdes' arms and my hands and back pressed against her small but firm breasts, arms and legs as they brushed against me. Sometimes we exchanged positions, but it was difficult for me to handle Lourdes weight and the high seat. One day Julie said she wanted to try and see if she was able to manage taking me 'doubles'. It was quite funny and we nearly crashed. I however enjoyed feeling Julie's breasts press against my back and hands.
A week into the summer camp and the girls asked me what I did on Saturday and Sunday afternoons as on those days I did not I did not go to the garage. I told them that I usually took a nap. They told me that they usually spent Saturday and Sunday afternoons reading comics, magazines, playing carom and cards or just chatting, on Julie's back porch. I told them that I would like to join them by 2,00 p.m. after doing the dishes and cleaning up the kitchen, which was part of my chores. They laughed saying that they did not know of many boys my age doing household chores. It seemed very "girlie" to them. We talked some more and they told me that they went for the 10.00 am swimming session that was "girls" only on Saturdays. They asked me if I could come to the club by late morning, as that was the time it was hot so most of the older boys and girls just 'hung around" playing tricks or jokes on each other. I told them that since I was free on Saturday mornings I would be at the club. I went to the club the next Saturday morning and palyed some indoor games for a while. By 11.30 am most of the smaller boys and girls had already left for home. The older boys and girls were playing catch with a volleyball and some were throwing balled up papers etc at each other. Lourdes and Julie were talking to Father Peter, regarding some program and Julie had left her bag with her swimming things on the bench. Some of the boys decided to play a prank on her and hid it. Julie made a show of begging them to return it to her. Eventually they showed it to her but instead of giving it to her they started passing it around and Julie started chasing it. She managed to get it, but lost her slippers in the bargain. Now Julie got fed up and gave them the other one too, saying they could have both. Fr Peter had already left and Lourdes now intervened. The boys started throwing it over her as she tried to block them. This went on for sometime until one of the boys in his excitement threw the slipper onto the ledge of the club house. The ledge was 10 feet high. To get to it one had to use a ladder. Lourdes got angry and taking a small stick started hitting the boys who made a run for it. They stood at a distance laughing and watched as Lourdes and Julie tried to retrieve the slipper.
I had watched the whole scene from a distance. I approached Lourdes and told her that if we could lift Julie up onto our shoulders, then she could use the small stick she had to pull the slipper off the ledge. Julie said she was wearing a short skirt and it would ride up her thighs. Lourdes asked me if we, Julie and I could support her on our shoulders. We tried but found her weight too much. Finally Lourdes agreed to make me stand on her shoulders. I was hesitant, so she asked if I was afraid of heights. I said that I was also selected to be the top of the pyramid, during our PT exercises. She said she could easily support my weight. Everyone present watched as she crouched on her haunches. Then she asked me to sit on her shoulders, putting my feet one on either side of her head. Now with Julie supporting me she slowly stood up. Then I slowly rose to a standing position. Lourdes held my legs for support. Now my eyes were in line with the ledge. Using the small stick I slowly retrieved Julie's slipper. There were also some shuttle cocks and tennis balls which I pushed down with the stick. I then slowly sat on Lourdes shoulders as she crouched down. Everyone present was amazed at Lourdes strength. They were also amazed that a girl had lifted a boy so easily. Some of the boys had earlier tried to retrieve the balls from the ledge but had failed. I too was amazed, but more thrilled to be lifted like that by a girl my age. I also realized that I like girls who were physically stronger than me. This incident brought us closer and more friendly.
So by the second week of summer club I was meeting Lourdes and Julie every Saturday and Sunday afternoons, between lunch and tea time, at Julie's back porch. Julie's back porch was an ideal place to while away the afternoons as it was wide, secluded, quiet. We played quietly for fear of disturbing anybody's afternoon nap. Her adjacent neighbors were Aunty Margaret and Aunty Rosy. At first we just played draughts or read comics and magazines. Then one day we decided to play cards on points system with the loser having to fulfill a forfeit.
We started with simple forfeits like hoping on one leg the length of the porch, staying still for 2 minutes, etc till one day, I asked Julie, the loser to climb the Guava tree. Julie hiked her skirts up and attempted to climb, while Lourdes and I had fun at her expense as she tried to climb in her tight skirt. Eventually she was able to climb till the main fork about five feet from the ground, but not before we had a good view of her underwear and thighs. The next day, Lourdes was asked to do a headstand. She was wearing a simple, short, flared skirted cotton printed dress. She tried to tuck her dress between her thighs but we had a good view of her thighs, underwear and all. We laughed it off, like good friends, telling her that for a slim girl she had nice thighs and buns, under her dress. Our forfeit started getting naughty and creative. The next Saturday afternoon Lourdes carried Julie cradle style and walk the length of the back porch. Lourdes easily lifted Julie and carried her in her arms. Lourdes was not even straining and proceeded to walk the length of the porch and came back, with Julie in her arms. She kept on holding Julie in her arms and did not show any signs of tiring. I now realized that Julie was enjoying being lifted by Lourdes. The way they looked, I knew that Julie was happy that she was in Lourdes' arms.
Lourdes whispered something in Julie's ears, but I was unable to catch it. They laughed and I told Lourdes that she was physically very strong, for a slim girl. Only some days ago she had lifted me on her shoulders. She said that was different but she could lift me in any style if I was willing. Before I could answer she grabbed me and I found myself being lifted off my feet in her arms. I could only wrap my arms around her neck in an instinctive reaction. My body started feeling pleasant sensations as I held on to her neck and felt her small breasts against my body. I was getting excited. The feeling was new. She carried me and started walking the length of the porch and back, asking how it felt to be carried by a girl. It was a pleasure, I could not describe, just being carried by her and I showed no signs of wanting to be put down. Julie asked me if I was enjoying being carried. I told her that I was not aware that I would enjoy being carried by a girl so much. This was different than when she had lifted me on her shoulders. Lourdes was still carrying me in her arms, when Julie said that I had to fulfill a forfeit now. I asked why and she said that Lourdes had done two forfeits and it was my turn anyway. She went to the clothesline and pulled off a dark printed dress that was drying out there. She said that it was a dress that she had stitched only last week. It was a simple A line dress with a round neck, very short sleeves and a flared skirt and it would fit me. I did not understand much of what she said, but realized that I was being offered a chance to wear a girl's dress. Meanwhile Lourdes still held me in her arms and she threatened to carry me outside to the street where a few boys were playing French cricket. I did not want the other boys to see me like that so I agreed and Lourdes let me down, back on my feet.
I was asked to remove my shirt, which I did, feeling shy and embarrassed to be half naked in front of the girls. I slowly took up the dress and was about to pulled it over my head. The girls pulled it around me. I cannot remember the details after that. Only I was excited beyond anything I had experienced so far. The girls told me to remove my short pants. Now I had only my thin underwear under the dress. The girls quickly started playing another round. Lourdes and Julie were enjoying what they thought was my 'discomfort'. I pretended to be at a discomfort but inside I felt elated that I was finally able to dress in female clothes. We played a few more rounds and I was unable to concentrate and lost. Lourdes and Julie both took turns carrying me, while I was dressed in her dress.. I was finally unable to control myself and I told them that I was excited and I was feeling like 'peeing'. Julie told me to hurry as she did not want me wetting her dress. I went to the toilet and realized that I was reliving myself standing like a boy while wearing a dress. I did not need to even jerk off as I was 'cumming' as soon as I lifted the dress.
After an hour or so they told me that I had been quite sporting and had worn a dress without a fuss. I pretended that I felt embarrassed. They said they would not tell anyone.
That night I went to sleep all excited and dreamt that I was dressed as a girl and I was enjoying myself with my 'girlfriends'. I woke that morning feeling the stickiness in my shorts and realized that I had been having "wet dreams".
Dressing on my own and with women, secretly – 3
We met up the next day again at Julie's back porch. Julie and Lourdes did not make any mention of my wearing a dress the previous day. Julie's mother was there too and she joined us in playing a few rounds of cards and draughts. Julie's mother was young and attractive. She wore a sleeveless thin cotton housedress that clearly showed her bra. I was her partner for most of the games and as we played she got excited and every time we won gave me high fives and touched my arms that sent goose bumps down my spine. I tried averting my eyes from her boobs and front but every now and then I just could not resist it. I did not know if her touch or her boobs were more exciting.
That evening I sneaked out to Julie's back porch. It was dark and I saw no one about. I saw the cotton house dress that her mother had worn lying carelessly on the clothesline. There was also a bra close to it. I went to it and touched it. It was exciting. I looked around and seeing no one took it and the bra from the clothes line. I did not know what I was going to do with it. I held it to my body and felt excited. I took it to the toilet and closed the door. My excitement started mounting and I forgot my surroundings. I removed my shirt and tried to put on the bra. I was unable to hook the bra at the back, but I felt it against my chest and my nipples felt a strange tinge. I put my hands in the sleeves of the cotton dress and pulled it over my head. I could feel a strange but exciting feeling. I hugged myself and started touching my body thru the cotton dress. My excitement mounted and I felt my penis ready to explode. I lifted the dress as my body shivered and my penis exploded with excitement. After a time I was aware of where I was. I pulled the dress over my head and removed the bra. I opened the toilet door and went and put the dress and bra, just as I had found them. My underwear was sticky so I went quietly home and changed. I realized that I had dressed in a woman's dress and bra and had cum.
I felt a little guilty every time I saw Julie the next week. I had "cummed" while wearing her mother's cotton dress and bra. By Saturday I was over my guilt feeling and joined Julie and Lourdes on her back porch. That day we did not do anything naughty. The next day Julie's mother again joined us and I saw that she was wearing the same dress. It excited me to see her in the dress that I had secretly worn. We started to play cards and Lourdes and Julie said that the losers should forfeit. By a strange coincidence Julie's mother and I kept getting dreadful cards and we kept losing. Finally Lourdes said that it was time for us to fulfill a forfeit. They were suggesting different forfeits which we kept rejecting until they said that I was to dress as a girl and Julie's mother had to wear her husband's clothes. I was about to object when Julie's mother said that we would do it.
The girls wasted no time and Julie quickly got together a brown pleated mid length skirt, a beige blouse and some other girly things, all ready for me to wear. Julie's mother said she would go in and change into a pant and shirt of her husbands while the girls dressed me. I was a little nervous and hesitant so Lourdes took charge and soon I was standing before them in only my briefs. Julie folded my clothes and then she proceeded to put a bra on me. I stood there obediently as she put the bra on me. She then took small balls of cotton which she stuffed in the cups. I felt small shiver run down my body as she adjusted the bra. Lourdes commented that I was already blushing, but not to worry. After this she lifted a petticoat over my head and onto my body. She ran her hands down my sides and back, adjusting and smoothening out the material over my slender frame, making sure the bra was secured in place. Then she helped me into the skirt and pulled the blouse over my head and onto my torso making sure the sleeves and neck were centered and the bra straps were hidden. They had me remove my slippers and wear a pair of Julie's mother's high heeled slippers. I tried to stand in them and nearly fell and they laughed at my discomfort. For my hair they used a scarf to hide my short hair. A little powder and light lipstick and they said that I was now very girly. Now that I was dressed they both started calling me Nicole.
There was no mirror for me to look at my image. Lourdes and Julie's reactions though spoke volumes about my appearance. Their remarks to each other convinced me that I was looking like a girl. Looking like a girl was one thing, but feeling like one was different. At first I felt my penis stir and harden, but after a while the sensation shifted to my nipples and fingers. Every time I ran the ends of my fingers on the material of the skirt and blouse I felt a queer but exciting feeling. The touch of Lourdes and Julie's fingers were also very exciting and my body was acutely aware of being touched. I was enjoying the sensation very much. My senses were now on high alert.
Julie's mother came back and she was dressed in her husband's pant and shirt. The girls told her that she did not look like a man with her boobs nearly bursting out from the shirt. She tried to make amends by tying her hair back tightly and removing her earrings, chain and bangles. Lourdes said that it would be good if I wore the bangles and chain and so Julie's mother started putting them on my wrist and neck. Since I did not have pierced ears she said she would get a pair of clip on earrings. She went inside and fetched them. She fixed them on me and said that it was a pity that we did not have a wig or I would look very pretty. The girls and Julie's mother were excited.
Julie and Lourdes suggested that we play a few more rounds dressed as we were. We then sat down to play again, only now I had to sit like a girl, careful not to let my skirt ride up my thighs. The breasts I was having obstructed my lower vision and I had to make some adjustment to my posture while dealing the cards and stretching. Lourdes and Julie were enjoying watching me try to behave like them. They kept touching my thighs and buttocks, saying "Nicole is sweet, Nicole is a good girl". We were so engrossed with our game that we did not notice Aunty Margaret approach. She said that she had heard some voices coming from Julie's back porch and was intrigued to find Julie's mother dressed in pants and shirt playing with her daughter, Lourdes the tomboy and another girl whose head was covered in a scarf. On coming closer she realized that there was something amiss with the girl with scarf. She was still guessing when Julie's mother told her how we had lost the games and were fulfilling the forfeit. Aunty Margaret looked closely at me and said "this can't be Dolores' son". Lourdes and Julie laughed and Aunty Margaret was amazed. With all this we were unable to concentrate and before I knew it they were saying the game was over and we had to forfeit again. I was still trying to figure out what the forfeit was when Julie pulled me to my feet. I was made to courtesy like a young girl. I was new to this and Julie and Lourdes took turns instructing me. Then I was shown how to walk like a girl. Finally Lourdes and Julie said that Julie's mother was going to give me a cycle ride. Aunty Margaret was enjoying this free spectacle.
In the meanwhile the girls took me by the arms and I was soon seated on the crossbar of Lourdes' cycle. Lourdes helped Julie's mother to sit astride the cycle. They held the cycle and encouraged Julie's mother to pedal. Julie's mother was riding a cycle after a long time and she was soon tired. Lourdes and Julie helped her dismount. Julie helped her to the porch where she and Aunty Margaret continued to laugh. Lourdes sat astride the cycle and told me to sit still. She was good on the cycle and she started riding around the backyard. Suddenly a mischievous smile lit her face and she started for the street. I tried to stop her but she continued and soon we were out of the lane on the street. The street was empty and Lourdes needed no encouragement as she quickened the pace. To say that I was nervous was an understatement, but within a few minutes I was able to enjoy and felt like a girl. I had to put one hand on my skirt to prevent it from riding up my thighs. The wind on my legs and face felt so good and Julie's mother's arms on either side made me feel secure. I could feel her breasts against my back and every now and then she let go of one handle and touched my shoulder.
We rode out onto the main street and towards the sea side. I was really excited. Here I was dressed as a girl and being given a ride on a cycle by a girl. I was enjoying myself so much that I felt a little saddened when we returned back after a half hour. Although it was sunny and hot outside I had not felt the heat in my excitement and I was now getting used to the skirt and was walking as instructed by the girls. Julie had prepared lemonade which we drank slowly. We were all excited and feeling naughty. Julie asked me if I was comfortable in her skirt and blouse. Lourdes said that of course Nicole would feel comfortable, Nicholas would be in discomfort. Aunty Margaret said that if she had known earlier she would have brought a wig along. We asked her why she had a wig and she said she had two wigs which she used sometimes..
Julie's mother said that she had quite a time and did not expect to enjoy so much. She told Lourdes and Julie that they were naughty to embarrass me by taking me out dressed as a girl. They said that no one had seen them and so it was okay. Julie's mother said that she was going in to change and asked the girls to help me undress. Aunty Margaret went to her house to answer a telephone call. When Julie's mother had gone inside, Lourdes suddenly held me from behind in a tight grip while Julie hiked my skirt up and pulled down my under wear. I was caught off guard and although I protested I did not resist. Lourdes and Julie exclaimed in delight on seeing my stiff penis. They said that I was really sexually excited to be dressed as a girl. They noticed my deep blush and did not want me to feel more embarrassed. Lourdes released me and told me to pull up my underwear and undress. It was time for Nicole to disappear and Nicholas to return.
They removed the bangles, necklace and jewelry. The scarf was untied and I was helped out of the high heeled shoes. After that they told me to undress on my own as they watched. I opened the top buttons of the blouse and pulled it over my head. The skirt had a hook at the back which I could not reach. They told me to turn it around so the back was in front and unhook it. I did as they said and stepped out of the skirt. Now I was only in the bra and I struggled to unhook it. They were enjoying my discomfort and teased me. Julie's mother came to my rescue and unhooked the bra. I felt such an excitement when she turned me around and helped me out of the bra. She went back inside after this.
While I was putting on my shirt they told me that they too were enjoying treating me like a girl. It had started as a joke but now they were enjoying just as much as I was enjoying. We started talking about certain places like Thailand where there were many boys who dressed as girls and looked very beautiful. We discussed about some events that we had read in the magazines and generally agreed that some males had certain female traits and so they dressed as females. We also talked about the "Hijras" who made their rounds in the market place, but they were very recognizable as most of the ones we saw had manly structures and voices. They asked me if I knew of other people in our neighborhood who did this secretly. I told them about the incident I had witnessed with Aunty Margaret, Aunty Rosy and Arthur. They listened with rapt attention but were not convinced saying that although Arthur looked good when he used to dress up as a woman for the fancy dress during any neighborhood socials, he was very masculine and had many girlfriends, Besides Aunty Margaret and Aunty Rosy were upright and sporting, but did not seem like the type who had masculine traits or dominating characters. Arthur had found a job in the Middle East some years ago and so moved out. Julie's mother called out for her to come in and help with some chores and Lourdes and I left. We all agreed that we had had a fun time.
I was otherwise enjoying myself as a boy, in all other activities. For the "club social" evening I went along with Julie and Lourdes and they showed me a lot of new dance steps including the jive (rock and roll). The local gym was the venue and it was jammed packed with other friends and teenagers so we just enjoyed dancing and having a good time. Lourdes and Julie were good dancers and they took turns leading me. No one noticed but I was thrilled that they were giving me the female part. During a break in the music we started discussing the coming week's program. There was a picnic, an open air movie screening and last of all a fancy dress competition. The mention of fancy dress immediately hit me and I looked towards Lourdes who was trying to catch my eye. She indicated to me that she and I were going to be a team in the fancy dress competition. I nodded and she smiled back. When the music resumed she immediately picked me up to dance and told me that she had already submitted our names for the competition. I asked her what we would be dressing as and she said she would come up with something.
We did not have to wait long as the next afternoon Aunty Margaret was at home and sitting on her back porch. A man too was there and he was tying together long sticks in preparation to remove drumsticks from the tree that was in Aunty Margaret's back yard. Since they were there we could not play our usual games and decided to just read comics. The man proceeded to remove the drumsticks and Aunty Margaret asked us to help him gather them. In a little while he had removed a large number and we had collected them. Aunty Margaret gave us each a rupee ( which was a lot at that time). The man was paid and excused himself saying he had some other work and left. Aunty Margaret then looked towards Lourdes and asked us what "this tomboy" was doing here in the afternoon. We said that we usually played cards or read comics or played hopscotch. When she heard hopscotch, she looked at me and asked if I too played hopscotch. I said yes, which surprised her. She agreed to join us if we played hopscotch and so we marked up the squares and started playing. After a little while Aunty Margaret got tired and said that for a boy I was very good at hopscotch. She told Lourdes and Julie that they should give me a dress or skirt as I was so good at playing hopscotch, which is considered a 'girlie' game. I blushed and she joked even more with Lourdes and Julie, that I should be given a dress to make me more comfortable. They joined in and agreed and egged Aunty Margaret all the more. Aunty Margaret had already seen me dressed as a girl yet she said that with the right clothes and makeup, I would look very good as a girl. Lourdes and Julie kept the discussion on by saying that maybe their dresses would not fit me, but most male who dressed as females at fancy dress events usually wore sarees. Aunty Margaret agreed saying that the saree covered their hairy legs and gave them a better figure that is why it was a favorite article for such events. She said that it required proper draping, like Aunty Rosy, who looked good in them. Finally Lourdes said that there was a competition at the summer club next week and if she would help then they would ask me to dress as a girl. Aunty Margaret agreed. Julie said she would go solo as a gypsy woman while Lourdes and I were going as a couple. Lourdes told her that she had dressed as an English Lord in their school play, complete with tailcoat, tophat, boots, pocket watch, moustache and cane. If she could find a long gown and wig then they could dress me as an English lady with parasol and all.
Aunty Margaret said that if we went to her home we could search among her old clothes and come up with some suitable items for our fancy dress. We went to Aunty Margaret's house. She led us to her bedroom, where I had seen her dress Arthur. From her cabinet she pulled out a large box and opened it. From within she removed different items and soon she had arranged a few sets of jewelry. She pulled out a large trunk from beneath her bed and from within removed a wide variety of dresses. Aunty Margaret, Lourdes, Julie and I were soon picking out items that could be used. There were evening dresses and other dresses, which Aunty Margaret had worn when she was a young woman. She complied a set of gypsy clothing, consisting of a red cotton flared layered skirt, with small yellow, white, green flowers at the bottom, a pink sleeveless tight short shirt, red scarf, red beads necklace, large hoop earrings, red bangles and red high heels. She added a stiff white layered taffeta type petticoat. She looked at Julie and asked if she was ready to try out the costume. In the meanwhile Lourdes and I continued to search out a suitable costume, from the trunk. Julie took up the costume and stepped around a small screen to change. Aunty Margaret went to help her and soon she emerged dressed like a gypsy. She posed in front of us and Aunty Margaret said that the costume was perfect and with the other accessories she would look great. Julie went behind the screen and changed back into her own clothes. She folded the costume and accessories and put it into a large plastic bag that aunty Margaret gave her.
In the meanwhile Lourdes had found a lavender gown with a tight small waist and flared skirt. It had buttons down the back and lace bodice, just like the dresses worn by young women in the 20's. Aunty Margaret asked me to stand and put the dress against me saying that it looked like my size. She found a nice layered long petticoat and said that with this under the gown I would look more womanly as it would fill my hips and behind. She asked me if I was capable of wearing the petticoat and dress on my own. I hesitated and looked at Lourdes, so she proceeded to dress me. She had me stand up and remove my shirt. Then she helped me into the petticoat. The petticoat was from the waist down so she asked me to step into it. Lourdes held my arms as I stepped into the petticoat. She drew it up to my waist and tied it tight with the drawstring. Then she said that I would need a small size bra. Both Aunty Margaret and Julie were big breasted so they looked at Lourdes. Lourdes went behind the screen and after a few minutes came out with her bra in her hand. Aunty Margaret guided my arms thru the straps as she fixed Lourdes' bra on me. This was not the first time I was wearing a bra, but this was the first time I was wearing a bra which was just worn by my friend Lourdes. I was thrilled. Aunty Margaret adjusted the straps and filled the cups with a little padding. I was already excited and visibly trembling, which Aunty Margaret noticed. Aunty Margaret and Lourdes now helped me into the gown. Since it was full length she drew it over my head. Then she asked Lourdes to hook the buttons at the back. The buttons ran all the way from the base of the neck till the middle of my bottoms, where a big bow was fixed.. I was acutely aware of Lourdes' fingers as she buttoned me and Aunty Margaret's touch as she adjusted the petticoat beneath the gown. When she was satisfied she noticed that the waist was loose, so she took some pins and tightened it. Now the gown looked good, with a tight low laced bosom, tight waist, full hipped skirt touching the floor and nicely fitted lace sleeves ending just below my elbows.
Aunty Margaret told me to relax and she found a pair of closed white inch high shoes. She asked me to try them on. They were a little loose, so she filled the toe with cotton and asked to try them on again. This time the shoes were comfortable. She asked me to walk around the room in them and I found that I could manage walking in small steps. The shoes were okay, but I was having trouble with the petticoats and gown. Aunty Margaret showed me how to walk so that the skirts swished without getting entangled in my shoes. I followed her instructions and she was pleased. She asked me how I was feeling. I did not answer. She knew as she had felt my body tremble with excitement while she dressed me. She said that she would continue dressing me completely, but would not put on the make up and jewelry today. She just wanted to get the costume ready now. She asked Lourdes to walk alongside me and made me practice walking as she rummaged in her cupboard and came out with a nice wig done up in the style of the 20's with a loose flat bun at the back. She touched it up and then she fixed the wig on my head. Satisfied, she put on my hands lace gloves which made me feel ecstatic. Then she gave me a small beaded hand bag, a dainty folding hand held fan and an old fashioned lady's wooden handle parasol. She showed me how to open the fan and fan myself bending my wrist, like a lady. When I tried it I found that this small gesture made me feel so feminine. After the fan she showed me how to use the parasol which again made me feel more feminine. Now she made me walk and guided me so that I was walking like a young English woman, swishing my hips and daintily fanning myself while holding the parasol in one hand. I was only to happy to follow her instructions and she was excited with the way I was responding. She told Lourdes and me that I was walking and standing better than most girls my age. She went on complimenting me so that I was blushing. Finally to prove her point she made pose in front of the mirror and I was surprised to see myself look so ladylike even without any makeup or jewelry. She asked Lourdes to stand behind me and gently hold my waist. When I felt Lourdes' hand on my waist, I responded by falling back against her. She was not wearing a bra so I could feel her breasts thru the fine material of her dress. She continued holding my waist with one hand and caressing my stomach and arms with the other. My excitement was building up and Lourdes sensed it. Aunty Margaret also sensed it and said she that I could get used to the gown while she prepared us some tea.
When she had gone to the kitchen, Lourdes turned me around and I found my knees getting weak as I leant against her. My cheeks rested now on her neck and I could feel her nipples harden. I was feeling so weak kneed with excitement that I started to lose my balance. She put her arms around me and lifted me up like a child. I was so relieved to be in her arms that I held on to her neck and shoulders. She carried me to a chair and sat down with me cradled in her lap. I was excited and thrills ran down my body. Lourdes sensed my excitement and held me in close. She motioned to Julie, who had been watching us. Julie came over to me and touched my cheeks. At that moment I felt a huge shiver and I knew that I was having a "cum". Lourdes too knew that I had "cum" so she asked Julie to lift up the petticoat and skirt of the gown. Julie did and said that it was alright. She quickly removed her kerchief and held against my bulge. I was still coming out in jerks wetting my underwear and shorts. I was shivering with excitement. When I was thru and she was satisfied that I would not stain the petticoat and gown she lowered them. Lourdes asked me to stand up, which I did on shaking legs. I was helped to another seat. We hurriedly composed ourselves Aunty Margaret came in with our tea. She asked me if I was comfortable with the shoes and gown. She said that I was already used to the gown. I said that I had to go home and Lourdes too said the same. Aunty Margaret poured out the tea and we helped ourselves to some biscuits. My hands still shook so I was careful not to spill any tea on the gown. We talked for sometime and then Lourdes said it was time for us to go to the club. Lourdes and Julie helped me undress and neatly folded the gown and petticoat. They smirked when they saw how wet my shorts were. I let my shirt cover the stain. Lourdes undid the bra and stepped behind the screen to get into it. When I was dressed in my boy clothes again, Aunty Margaret said that she would help me dress on Saturday for the fancy dress competition. I agreed and we had our tea and left. Lourdes said she would arrange her costume too. Once outside I looked at Lourdes and Julie and they looked at me too. We knew that this was more than just fun for me and they had hit upon a secret desire of mine to dress as a girl. They knew that I was getting immense sexual pleasure from wearing female clothes. It made me feel light headed and I felt very feminine. When dressed I was more docile and easy to handle than when I was in my male clothes. We shared a secret. I was their "girlfriend".
With this new knowledge in mind I went home and bathed and went to the club dressed as a boy and behaving like one. I met up with Lourdes and Julie and we played a few rounds of table tennis. On our way home Lourdes said that she had a new white bra and cycling shorts that she wanted me to wear tomorrow under the gown. Julie had brought me some nice white ribbons and self colored knee length silk stockings. I thanked them for the items. That night I slept with the new bra, silk stockings and ribbons under my pillow.
Curiosity, walking down a secret road.
The next day was Friday and I went with Lourdes to her school to get her costume. The sister in charge was happy to see her and told her to return the costume as soon as possible. On Saturday I informed my Mother that I had taken part in the fancy dress competition. She asked me what I was dressing as. I told her that she would be surprised. She asked me why, so I told her that I was dressing as an English madam from the twenties. She looked at me in surprise and said how was I going to become one as she did not have any such fancy clothes. So I spun a tale of how a group of my friends had challenged me and Lourdes to enter the competition and go as the opposite sex. We had approached Aunty Margaret who had arranged a nice old fashioned gown and accessories for me. Lourdes was borrowing an English gentleman's costume from her school. We planned to dress at Aunty Margaret's house, but it was quite a distance to the fancy dress venue and we were afraid of getting all hot and sweaty, so Aunty Margaret was arranging for us some sort of transport. I needed some money for a film roll for Julie's father's camera. My Mother said that since we had not gone on holiday this year she would give me the required money.
That evening was one I will not forget. I went to Aunty Margaret's house at 4 pm, The program was to start at 6.30 pm. That would give Aunty Margaret enough time for her to dress me up and put on my make up etc. Aunty Margaret was expecting me and had altered the waist line and pressed out the gown so it looked much better now. I showed her the items Lourdes and Julie had given me and she smiled. She asked me to strip off my shirt and pants and noticed I had worn tight cycling shorts inside. I told her that I had worn double underwear and the tights as I had got excited last time and nearly stained her petticoat. This brought a knowing nod from her. After that she concentrated in getting me prepared and I was thankful that I had worn double underwear as it was even more exciting than the first time as this time she had to help me with the silk stockings too. All along she did not let me see myself in the mirror. She had me wear false eyelashes that at first blocked part of my vision. She told me to open my eyes a little more and it would be normal Only when she had done my face up and decked me in a fine set of imitation pearl jewelry and sure I was transformed into a comely English madam did she guide me to the mirror and let me enjoy looking at myself. I was surprised at the transformation. She had made me look so feminine, that already I was feeling soft and docile. I could not believe that the red lips belonged to me and my eyes were looking like that of an actress with the false eyelashes. I tried batting my eyes and smiled at the effect. The little hat with ribbons that sat on top of my head was a nice English touch. As I was admiring myself she said that since I was dressed she would take some pictures with her simple box camera. For that we would have to go outside as she did not have a flash. She lead me to her back porch where there was enough sunlight for a good picture.
Walking out was such a pleasure, the soft petticoat and gown swishing around my legs. I was already feeling heady. I was also feeling light headed and was ready to do whatever Aunty Margaret wanted me to. Aunty Margaret took pictures of me sitting, standing, with the parasol open, fanning myself with a dainty folding hand fan, leaning against the railings, etc until Lourdes and Julie arrived dressed as an English gentleman and a gypsy woman respectively. We clicked some more pictures which I was hardly aware off as I was now so happy and behaving like a Lady. Then she went inside and hurriedly dressed and started leading us through her front door where Mathias uncle, who had an Ambassador taxi was waiting for us. She asked us to get in the back seat while she sat besides Mathias uncle. Mathias uncle was all smiles looking at the three of us dressed in our fancy dresses. He guessed that Julie was the gypsy woman but had no idea who the Englishman and woman were. It was not such a long distance by taxi, yet all the way he tried guessing who we were.
We arrived early and Lourdes went to confirm our participation to the MC for the evening. Aunty Margaret fussed a little with my costume before going to find her way in the audience. We were taken back stage and given our numbers. In a little while the competition started. There were two groups, juniors up to 10 years and seniors 10 years and above. All the participants had taken a lot of trouble with their costumes and their introduction line. I had not prepared any but Lourdes said she would answer for us. I was so into being a woman that I clung onto Lourdes's arm like we were an old fashioned honeymooning couple. The other contestants were looking at us and trying to guess who I was as some of them guessed that it was Lourdes in the tailcoat. They had no clue as to who the attractive Englishwoman was. I did not speak only batted my eyes and smiled at them. My whole being was so pleased to be out dressed as a woman that I was having a pleasurable time. In the meanwhile we were told to sit in the wings according to our allotted numbers. One by one the numbers were called out and we could hear as the MC asked them to introduce themselves and say a line a two about what they had dressed as. The audience were enjoying themselves and we could hear loud applause and laughter at some of the witty answers. Finally it was our turn. I hooked my right arm in Lourdes' left arm, opened my parasol and held it in my left hand, and let the purse hang from my left wrist. I gave the parasol a slight twirl as we entered the spot lights and made an elaborate show of fanning myself daintily. Lourdes walked slowly thumping her cane and I sashayed besides her just like I had seen the woman in old movies do. The MC was saying that he did not recognize this couple and that maybe we were in the wrong place to which Lourdes smiled and I batted my eyes and pouted my lips. The MC asked the audience if they could guess if we were both girls dressed as a couple. Lourdes and I did a round of the stage and then a mike was thrust at us, which Lourdes took. Lourdes twirled her moustache and said "This MC is not feeling well, he cannot recognize a woman and a man, calling us girls, We are Lord and Lady Wentworth and everyone can see who the gentle man is and who the lady is from our dress". She added with disdain "get on your knees and greet Lady Wentworth". The MC went on one knee and I curtsied, spreading the skirt of my gown with my right hand and bending slightly at the knees. I extended my gloved right hand for him to kiss, pouting my lips and batting my eyelashes, but Lourdes pushed him with her cane saying in a loud gruff voice "that's enough you clown, where is your hat and why are you dressed in those funny clothes. Do you have any fashion sense at all, greeting my wife like a Romeo? Get on with your job, don't you see we are royalty from Great Britain". That brought a great applause from the audience. Lourdes beckoned me "come my Lady" and extended her arm for me to hook into as we walked away from the startled MC. The audience applauded once again and the MC hastily called out the next contestant. We took our place next to the previous contestants on stage and it was only then that I looked at the audience and realized that I was not only dressed as a woman, but was in front of a large audience, who were still not sure if I was a girl or boy beneath my costume. It thrilled me to know that I could pass off as a woman so convincingly, with hardly any practice. I saw Aunty Margaret in the front row and she caught my eye and made an O with her forefinger and thumb, indication all went well. I once again curtsied, spreading the skirt of my gown with my right hand and bending slightly at the knees. She waved back happy with my acknowledgement of her handiwork.
After all the contestants had been called out we were all asked to once again come to the front individually, while the judges prepared the results. Then we were once again told to sit in the wings behind the stage. It was only when we were backstage that the warmth of the summer night hit me. I had been wearing a wig, long gown and silk stockings in summer and now my petticoat and bra were beginning to get wet with perspiration. I had not had a drink of water for nearly 4 hours and my lips were feeling parched. Julie joined up with Lourdes and me and just then Aunty Margaret came backstage and offered us some soft drinks. I sipped the drink slowly like a lady and Lourdes and Julie were impressed. Julie said that almost everyone in the audience and most of the contestants had guessed that Lourdes was the English gentleman, but everyone was still wondering who the Lady was.
Finally the chief judge came on stage and thanked all the contestants for the efforts and creativity put into making the costumes. He said that he was having a hard time figuring out the gender of some of the contestants, especially the ones who had dressed in sarees. Some girls and some boys had worn sarees, but they all looked very feminine. He said however that the girl acting as the English gentleman was very convincing. The English lady was also nice, but not a difficult act for a girl to perform. At this some of the audience said that the English lady was a boy. He checked his list again and said that the entry was made as Lourdes and Nicole, both girls. We had been hearing him speak and we saw Aunty Margaret go to one of the judges and complain. The judge beckoned the chief judge who apologized and said that there was a mistake and that for a boy to act as the English woman was excellent. He said that they would have to reassess the points, keeping in mind that the Englishwoman was a boy. The audience applauded and in a few minutes the MC came on stage and joined the chief guest in announcing the winners. First the juniors were announced and with each prize the audience applauded. Julie's name was called out and she went up to receive a consolation prize. The boys at the back whistled and applauded loudly. Then the 3rd prize and the 2nd prize were announced. The prizes went to a boy and girl who dressed as an Uncle Tom and his wife, and to a girl who had dressed as a fisherwoman. I was beginning to feel dejected when they announced our names as the winners. Lourdes hugged me and we went on stage once more to receive our prize. The chief judge looked me up and down and said that even from close up he was not convinced that I was a boy. He added that had I not been 'married" to Lord Wentworth, he would certainly have fallen for me. I just batted my eyes and smiled at him. There were a lot of pictures taken and then the MC called out the final thanks to one and all.
The audience dispersed and the contestants now mingled with some of the audience who were hanging around. Some of the contestants had gone back stage to change their costumes. I however had no change and so waited for Aunty Margaret to come fetch me. Although I was feeling hot I was in no mood to undress. We were joined by a group of friends who all "Aahed" and "Oohed" at us. The girls were all amazed at my transformation while the boys wanted to know if I was free for a date. The girls kept touching me while speaking as though I was one of them. Some touched the small hat with ribbons that was neatly attached to my wig. A couple wanted to know what I had worn underneath that kept my gown so full skirted. I lifted the gown and showed them the layered petticoat. When they saw the petticoat and silk stockings they asked me how I had managed to stay poised on such a hot evening. The summer club volunteers said that they were putting off the lights and closing the auditorium, so we all moved outside to the benches besides the school ground. It was much cooler outside. But now we were surrounded by a group of pranksters and they started teasing me. Lourdes stood up and kept them at a distance with her cane. They however continued speaking from a distance. We started for home walking slowly as I could not walk fast. Aunty Margaret joined us and the group of prankster saw her and left us. Lourdes removed her tailcoat and hat saying it was hot and gave it to one of the girls who was walking along with us. Aunty Margaret knew that I too was feeling hot so she asked me if I was alright. I told her that I was hot and the petticoat and stockings were now sticking to my thighs and legs. Just then an older boy, who worked at the local garage, happened to pass by on his Lamberata (motor scooter). Aunty Margaret stopped him and asked him to give me a lift. The boy stopped and I sat sideways on the pillion seat and Aunty Margaret helped me gather the petticoat and gown so that it would not fly around. I held his waist for support and he took off. He did not know I was a boy and was pleased to give me a ride. All the way he asked me all sorts of questions. But I held his waist in one hand and the hat and wig in the other. The boy dropped me off at Aunty Margaret's house, where I waited for her and Lourdes and Julie to come. The whole evening was so much fun that I had not noticed how many times I had "cum". I walked to the back porch of Aunty Margaret's house and there lifted up the petticoat and gown and pulled down my tights and underwear. My underwear was soaked with "cum" as well as perspiration. I was deciding what to do when I heard the sound of the others approaching. I hurriedly pulled up my underwear and tights and let down the petticoat and gown and went to the front door. Aunty Margaret was opening the door and Lourdes and Julie were joking and saying that they were worried that the boy would run off with me.
Aunty Margaret ushered us into her house and put on the ceiling fan so that we would cool down. Then she asked Julie to help her with some refreshments. While they were in the kitchen Aunty Marci knocked on the door. She was surprised to see us and more so as we looked like two females only one was dressed in a vintage gown while the other was dressed in a shirt and trousers. She asked for Aunty Margaret. Lourdes told her to sit as aunty Margaret was in the kitchen. Aunty Margaret heard her and came out into the sitting room. Aunty Margaret told her that we had just come from the fancy dress competition, that is why the old fashioned clothing. Aunty Marci was the active member of the church Lady's sodality. She said that she was happy as she needed three girl volunteers for tomorrow's senior female citizen's monthly lotto at 6.00 pm. Aunty Margaret said that we were free and would help. Aunty Marci thanked her and said that we had to collect the lotto material from Sister Rita at the church hall by 5,30 as she had to go for a retreat.
Aunty Marci said we were good girls and then it struck Aunty Margaret that Aunty Marci only wanted girl volunteers, but before she could correct her mistake Aunty Marci was already walking out saying she would inform Sister Rita. When we were alone I told Aunty Margaret that I could not go as I was not a girl. Aunty Margaret considered it and then said that maybe I could be a girl for one more day. I told her that dressing for the fancy dress was one thing but dressing as a girl and helping in the senior citizens lotto was another thing altogether. Lourdes and Julie said that I had been so well behaved and genuine as a girl, that surely I could do it for a good cause. They agreed to be with me at all times so that I would not be embarrassed. And so it was that while I was still dressed as an English woman from the twenties that I had to plan to transform into a teenage girl in the seventies.
Aunty Margaret said that she could open up the bun on the wig and she had an old dress that she had not given away which would fit me with a little adjustment. With these and a little make up I could look better than most teenage girls. Saying this Aunty Margaret took me by my hand and led me to her bedroom where she proceeded to undress me slowly. I tried to help, but she stopped me saying that an English lady should have a maid. Lourdes and Julie joined her and they laughed. She took her time undressing me and was surprised that I had not complained about the heat or sweat as my petticoat, bra, silk stockings and under wear were all wet with sweat. She undressed me till I stood in the only the heels and my tights. I felt relieved when she pulled off the stockings, but she put the shoes on my feet once again. She removed the hat and jewelry, leaving only the small earrings. Then she went to the cupboard and removed a dress with a black straight skirt and grey blouse. made no move to remove the small hat, wig or jewelry. Instead she led me to the mirror. I just followed her and she suddenly tugged off my tights and underwear leaving me naked. She came up behind me and kissed my neck and ears and reached around me and touched my penis, which jerked in response. She held it tight and slowly stared caressing it. Slowly her movements grew faster till she jerked me so that I came in spurts. I leaned against her. I felt shy and blushed, but she already knew that I had been wetting my underwear the whole evening and was ready for more. She turned me around and kissed me and I nearly fainted with excitement. She lifted me up and carried me to the bathroom. She told me to sit on the plastic stool that was there and she pulled off the shoes and silk stockings. She unpinned the small hat and wig, removed the necklace and jewelry and washed off the makeup. When all trace of the make up was off she started bathing me. I was totally helpless and sat there like a young girl as she bathed me. She washed me all over, even my private parts which got me excited again. She washed my private parts and all the sperm. Then she took a towel and started drying me. When I was dry she once again lifted me in her arms and carried me to the bed. I lay naked as she powdered my body. She pulled out a tight lady's underwear and helped me into it. I was wondering what else she had planned for me when she said that I had behaved like a sexy "Lolita". I did not understand so she said that she would explain some other time. She said I must be tired and it was getting late. She asked me to wear my shirt and shorts, while she prepared some soft drinks for us. While we were drinking the soft drinks she said she would wash off my underwear and tights and take care of the petticoat and gown. I said I did not know how to thank her for a wonderful evening. She said there would be other times. I kissed her cheek and then left for home.
Aunty Margaret had called me "A Lollita"…. And I wondered as I drifted off to sleep.
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