Story of How I became a Shemale from a Crossdresser

Hi friends the following story is by one of our fans. I am a 33 years male to female crossdresser. I was crossdressing since my college life. I dont have parents. I have been brought up in an orphanage. From my childhood, Internally I felt like a woman. When I passed my graduation I worked in a firm. A retired army man(widower) was running that firm. I worked there as a data entry operator. He provided me a room in his house. I stayed alone.When I was alone in the room I used to apply make up on my face like a female does. I have wigs , saree, salwar suit and jewellery. I had already pierced my both ears. I am very happy to live here Because there is no disturbance.
On one Sunday, I was in my room and had applied heavy make up on my face. I was watching movie in my TV. I forgot to close the door. Sudddenly my boss came to my room. When he saw me he was a bit confused to recognize me and asked me who am I. When he listened my voice then he realized who was it. I was very much nervous to see him.
But he told me not to worry , he will not tell anybody. You are looking so beautiful. One condition if you wear ladies clothes in the office then I will not tell anybody. Initially I denied but I had no way . Because if he kicks me out then I’ll be unable to get my bread also.
So I told him I am ready to do that but only after the sweeper goes back after cleaning the room. In our office I am the single employee.Next day the sweeper cleaned the office in the morning the left. After he left, I came to the office as a lady.
I was wearing blue saree with matching blouse. I have breast forms which give me good cleavage. I have smooth body and face without a trace of a single hair. We enjoyed a lot inside the office. After one month my boss decided to remove the sweeper.
After that entire time I used to live like a woman. But everytime it was not possible to live there as a woman. Some of the labourers were also working there. After 15 days my boss decide to keep me in his home.
He was living alone. His son was working in USA. In his home there is no problem for me living like a women. I do all the house hold work like a lady does. cleaning the room, clothes and making food also. I enjoyed this part of me. We also had sex every night. I lived there as his wife. I used to wear sarees and in the night, I used to change into nighties.
He had a very good stamina for sex. He purchased lots of sarees , jewellery, custom for me. Almost everyday I sucked his penis & did oral and anal sex with him. He gave me some hormone pills for developing my boobs. Even I did my hair removal surgery. Due to taking hormone pills my natural boobs increased, so I stopped using breast forms.
It continued almost 10 years, my hair was developed like a woman, and some times I went outside as female . When his son come to India, I moved to farm house. He stayed only for 5-10 days. His son thought I was a trustable care taker.
He never recognised me as a crossdresser. once my boss went to America for a long period. I was staying alone in the home. I felt lonely. Once I called our driver to my home. Before he reached the home I was fully dressed like a woman. I was in a green saree which was a bit transparent. I was wearing a tight green blouse which had deep back and deep neck cut which revealed my cleavage.
When he reached I called him to our room. He was unable to recognize me. After sometime when he recognized and was surprised. He is just 20 years old, I saw his penis erect. He is a tall handsome guy around 6′. I was unable to control my self. I never sex with any young guy. I gave him some coffee.
He touched my hand and unable to control, he started kissing me on my check. Then we went to our bed room. He pressed my natural boobs. Both of us removed our clothes and were fully naked. He licked my whole body. I started sucking his 8″ penis. He inserted his finger in my ass hole.
I was very much excited to see his tight penis. Then he started to enter his penis my ass hole. He fucked me really hard and after 15 minutes his sperms fell in my ass hole. I enjoyed a lot. From that day I told him to stay with me at night.
Now he rarely stayed in his room. It continue for around 1 month. One day he came to my home with two friends staying with him. One is 20 years and another is 18 years. Both are students in a local college. They belonged to same place. Due to higher education were staying here.
Our driver introduce them to me and told that they are ready to pay me for having group sex. We enjoy that night too much. I sucked their cocks and had sex. From that night they frequently visited my home. We would even go out in our car also. When my boss came to India I was unable to have sex with him.
After 6 months my boss decided to sell his property and move to USA. I was in a dilemma because from the past year I have been staying as a lady. Now I am no longer a crossdresser, however I have become a shemale due to all surgeries. I have natural 34 size boobs, hair like women, no facial and body hair but I have a penis. Now I can’t go back to my male avatar.
Finally he sold everything. I discussed this with the driver and started staying with him. I lived there like his girlfriend in his home. But some days later the college boys brought new boys for sex. He even collected money from them.
Now i am a fully sex worker. Basically the teen age boys come here and have sex with me and pay me good.