Describe your own best cross-dressed incident : Mr. Saha is my boss. Shantala is his secretary and I am, or I was, a young engineering trainee working directly under Mr. Saha. Most of the other staff (men and women) in our small firm are diploma holders and are not very good at dealing with customers and public. So that part of the job was left to the three of us.
One month ago we had held our twenty fifth anniversary and had invited our major shareholders, customers and leading public figures. Since such functions need a pretty hostess to make the necessary announcements, garland the VIPs, get candles for lighting the lamp, carry the tape-cutting scissors and bring in trophies, medals and certificates for handing over on the stage, we started looking for an outside person. We realised that such people ask a very heavy fees.
One evening, after office, we were discussing the arrangements and I was fooling around trying to imitate how the expensive hostesses would walk and talk. My tone was so convincing that our boss said he wished I was a girl. Then he could have saved on the expense of hiring a hostess. Shantala looked at me and said, "Boss, if you agree I can convert Manoj into a pretty girl." I laughed and said, "Shantala di, why don't you become the hostess?" Shantala laughed, "Do I look like a hostess?" It was true. Shantala is a fat lady and on the wrong side of forty. She has a daughter as old as me.
Our boss found the idea of my becoming the hostess, very funny. I realised he was serious when he told Shantala that she could work on me during the following two days, it being a weekend. He would meet us on Sunday evening and if he found that I could pass off as a hostess then he would pay me at least half of what the outside hostess would have charged. That meant almost two month's salary as extra income for me. Now I was really interested and decided to try it out.
A little after that, Shantala and I left office. I sat on the pillion of her two wheeler and we went to the mall inside the city. She bought a big jar of hair-removing cream and some costume jewlry with clip on ear-rings. Then she bought a lady's wig for my head size, explaining to the saleswoman that I was to take part in a play at the office.
That night as instructed by Shantala, I checked the cream on the back of my hand for any allergic reaction. There was no problem. Next morning I applied it all over my body except around my eyes and on my head. After my bath I could see that all the hair from my body was gone and my skin felt soft and nice.
Being a slim and trim twenty one year old guy, I had a fairly narrow waist of 26. I was curious to know how Shantala would manage other parts of my body to make me a girl. I took a rickshaw and reached her house by seven am on that saturday.
Shantala's daughter worked in a metro city and lived in a hostel there. Since her hostel room was very small, she had left most of the things behind at her parents' place. Shantala took me to her daughter's room and asked me to make it mine for the next two days. She asked me to go into the bathroom and take off my clothes and change into her daughter's casual clothes kept there. I went in and changed into panties, bra and a pink nightie and came out.
Shantala asked me to stand in front of the full length mirror at the dressing table and tell her what more I lacked as a girl. When I looked into the mirror I found my smooth and shapely legs below the nightie looked quite girly, but my chest was awfully flat. I put my arms on my chest and looked at Shantala. She smiled and she asked me to take off my nightie and bra. She used a special glue to fix a shapely pair of breastforms on my chest. The breasts felt heavy and sagged just a bit. But as soon as I wore my bra once again, my breasts held up and my nipples stood up proudly. The weight of the breasts had also shifted to my shoulders which was more comfortable. This time when I looked at the mirror, I knew my buttocks were looking too boyish. Shantala gave me the special padded panties which not only gave me nice buttocks but also managed to smoothen out my crotch in the front. This time in the mirror, I could see I was a girl below my neck. My breasts held in the white cups of the silk bra looked mature and full, my waist was as narrow as a teenager's and my panties for all appearances held nicely curved butts. The exposed skin all over my body was smooth and shiny.
I let Shantala work on my face for a while. She plucked my brows and applied foundation to my face and patted it in, with a coat of powder. Then she fixed false eyelashes and applied lipstick to highlight my eyes and lips. She asked me to wear the ear rings, neckchain, finger ring and bangles which we had bought the previous day. Last to be fixed was the wig which gave me straight hair reaching the middle of my back.
Shantala now suggested that I should wear a pair of faded blue jeans and a sky blue chicken kurta which belonged to her daughter. The jeans hugged my legs well and the light translucent kurta hung loosely on my shoulders revealing the outline of the bra holding my good sized breasts. I knew I was looking nice.
"Looking like a girl is just one part of the change", Shantala told me,"From now on don't ever forget that you are a girl. My husband went out for a walk just before you came. He will be back anytime now. I have told him that one of our daughter's friends will be here with us for the weekend and will be using this room. You are a girl for him. You have to behave as a girl in this house. Incidentally your name now is Mandira and it would be better if you could call me aunty."
Now I was afraid. "Aunty, please! I feel nervous." She hugged me to her large bosom, let her fingers pass through my long hair and said kindly, "Don't worry! You will be fine!"
***
"Uncle, please have one more toast..." I was telling Shantala's husband as I served him breakfast. He smiled at me and said, "Mandira, you remind me so much of my daughter and I can't say no to you...Why don't you sit here next to me so that I can put a little toast and jam into your mouth as I would have done with my daughter."
I felt shy and happy as I sat in next to uncle and he fed me. We kept laughing and joking and Shantala looked on approvingly.
Later in the day, uncle suggested we go to a cinema in the city. I tried to talk him out of it but he kept insisting.
So I changed into a blue salwar kameez and wore a pair of shoes with two inch heels. I sprayed a little perfume on myself. As I looked into the mirror I noted that I needed a bindi, which I did not need with the jeans. I fixed the bindi and tied my hair in a pony tail. Then I freshened my lipstick. As I walked across the marble floor of the house towards the main door, I thought the clik-clop sound of my shoes was typically girly and cute. My hips had begun to sway a bit now and my arms swung inwards with a bend at the elbows.
As I moved into the front seat of the car, uncle leaned forward and kissed me on my forehead saying,"My baby is looking very pretty and smelling very nice." For all practical purpose he was thinking I was his daughter. I felt very much a teenager next to him.
The movie was nice except that I had to change seats once to avoid a guy who was trying to play footsie with me from behind. Of course I gave some other excuse to uncle so that he will not pick up a fight. During interval, Shantal remained in her seat while uncle and I came out. He went to the loo. I was about to follow him. Then I realised, this loo was not meant for me. The ladies loo was crowded. So I went to the canteen to collect the free pop-corn against our tickets. A guy was giving one free sample of a new lipstick brand to the girls in the queue. He asked me to choose one from among the five colours he had. I applied each to the back of my hand and selected one. The guy smiled and said I had made a good choice and my boyfriend would love it when I wore it. His body language and smile was saying, the boyfriend would love to kiss me with it.
I suddenly realised that as a pretty young girl now, everyone would expect me to have a boyfriend. The idea was both nice and revolting. I liked uncle treating me as a girl, but a boy of my age would not only love me, but would think of sex with me. I could not accept the idea. "Yuck" I said to myself. Just then a boy standing behind me said, "So, do you have a boyfriend?" I turned and found a boy whom I recognised as Shantala's neighbour. "I beg your pardon..." I said formally as if I had not heard him. He smiled and said,"...the lipstick guy said your boyfriend will like your choice..." "oh that..." I replied and turned my head a bit haughtily. My hair swung as I turned my head and I was not sure if I had hit the boy's face with my hair.
"Hey I am Shantala aunty's neighbour. I saw you with them today. My name is Sachin. What is your name?" I had to struggle for a moment to remember my girl name but then I smiled and said, "Mandira..."
"Not Mandira Bedi I hope..." He tried to joke and extended his hand for me to shake. Even when he said Mandira Bedi, I knew he was looking at my breasts. But I sort of liked the attention. After all you can't blame boys for thinking of sex when they are looking at a beautiful girl like me.
Oh! Now I was really thinking like a girl. I even found it ok that a nice boy like Sachin was caressing my boobs with his eyes.
After collecting the popcorn bags, I wanted to use the loo. Sachin held on to the bags for me while I went to wait for my turn, among the ladies. Inside I found most ladies refreshing their lipstick. I did the same with my new lipstick. When I came out in a while, Sachin noticed that I was wearing the new lipstick. He said," If I now say your new lips are sexy, do I become your boyfriend." I smiled and said, "No sorry! That is too easy. You will have to work harder for becoming a boyfriend." Clearly, I was now flirting with Sachin. Our fingers remained in contact for a while as he handed back the popcorn bags to me.
When both of us went back into the theatre, Shantala was smiling from ear to ear. She was tickled to see that so soon I had manged to find a boyfriend. She forced Sachin to sit with us as there was a vacant seat next to me.
Sachin was too happy to sit with me. He leaned across me to talk to all of us. His shoulders repeatedly brushed my breasts. Both of us pretended not to notice it. At one point when Shantala and uncle were talking to each other, he put his lips to my ears and said, "I think you need nail polish to match your lipstick. If I buy you that, will that count as working hard to become your boyfriend?" I blushed thinking that I should have, on my own, thought of painting my nails, but he took my silence and blushing cheecks as a 'yes' answer to his question and said, "After the movie is over let us do just that. Tell them I will reach you home on my bike."
***
Shantala took me aside and wanted to know if I really wanted to go alone with Sachin. I nodded my head and she let me go, wishing me good luck. Sachin owned a Bullet and with my short kurta and parallels I could have sat with my legs on both sides of the pillion. But I decided to sit sideways and place my hand on his shoulders for support. As the bike moved I waved out to Shantala and uncle. They waved back with uncle making the victory sign with his fingers.
It was nice going into the mall along with a Sachin. I could see that many girls were looking at me with a little jealousy. Sachin was atleast six inches taller than me and well built. I held on to his muscular arm and asked him to walk slow. He tilted his head towards me and said, "Yes my sweetheart." I pretended to be angry and said, "I am not your sweetheart," "No problem, I know you can't say no no for long." I pretended to hit him for that while I secretly admired his confidence.
It was very nice experience for me to have the sales girls call me as madam and try to sell more things than what I wanted. I refused to buy anything but the nail polish as I did not want Sachin to spend too much on me. Though I had my hand bag, I was sure he will not let me pay.
After we bought the nail polish, I insisted on buying him some icecream. He joked with me saying, I should be careful about icecream if I wanted to maintain my nice figure. I told him I was counting on him teach me nice exercises.
After ordering, we sat near the glass wall of the ice cream parlour and looked at all the activity in the mall outside. Many girls like me were walking around, Few had boys or parents with them.
While we waited for the special ice cream floats to be readied, Sachin wanted me to start applying the nailpolish. I thought I would do that to please him. But having applied the polish I did not want it to spread while eating ice cream. I had no choice but to let Sachin feed me. Halfway through I realised he had actually tricked me into this situation. I smiled at him shyly and said, "You win..." He understood what I meant.
***
While Shantala made me look like a girl, uncle changed me into a doting niece. But Sachin did the most for me. Sachin made sure I fully became a young girl and turned into his sweetheart. By Sunday evening, we had met several times and spoken over the phone endlessly. I was now so much a girl that it was not a surprise that my boss readily agreed to my being the hostess. Before the event Shantala had to teach me to wear sarees specially stitched to maintain their folds perfectly while the hostess worked hard to please the guests. The trick was to make the saree look normal and naturally well draped over her nice curves, yet allow her to do all the work without it coming in the way or falling off the shoulders. It should also leave no one in doubt about the size of her breasts and butts without actually revealing it. It should reveal as much of her waist as posible. I also had to learn to walk in a slightly seductive and stylish way. I continued to live as a girl at Shantala's house till the day of the function and did my office work through remote access. On the day of the function, only a few of the staff realised who I was. I knew I was pretty as a hostess because many of the VIPs kept ogling at me during the function and sought my company after the function. I could even feel them staring at my back through the spagetti straps of my blouse. They also wanted me for their own functions. I continue to live with Shantala and work as a hostess most of the time. My boss has started a new line of business of supplying hostesses. I am also spending time with Sachin. I confessed my secrets to him but still he wants me as his wife. I must change fully to marry him. The thought that, one day I may actually be opening up my legs for him, no longer revolts me but makes me blush with a kind anticipatory shyness.