This is going to be really long excerpt from my life. Those expecting for a quick jerk off material then this is not the story you’re looking for. For novel readers, I did my best. I have given detailed description of events that happened, just for my love of writing. More importantly I haven’t cooked up anything, hence everything I have written is exactly what that happened. So i even decided to write the trial and errors. Enough of disclaimer let me introduce you to the story. I am 27. My kinky mind vanished as soon as I met this girl who became my wife. She meant world to me, although disastrously she passed away in an accident, along with my FIL. My MIL barely survived with multiple fractures. The disastrous event was one of the biggest traumas of my life; that which totally changed me. She was everything I wanted from a woman; she was faithful, loyal, very affectionate and always was by my side. Hence I wasn't looking at any other women sexually as I used to before. In fact, marrying her made me more rich. I was employed with Central govt, and she was the only daughter of a very successful businessman in my community. So the entire asset came under my control. Since the day my wife died, I became socially aloof. To overcome the trauma I asked for a transfer to Assam which I got; it definitely helped me but not my attitude. Whenever I moved out and saw couples I got instant outburst, sometimes I got annoyed, other times, I wept silently and even felt jealous. I began hating life as I felt there was no purpose for my existence. . I stopped supervising the businesses I got from my in-laws and let the managers have full control of the enterprises. I wasn’t having the high profit motive anymore. This was also the moment I decided to take VRS and do something which I liked. I was fond of designing a dream villa. But my work was made simpler because of a friend who was running a construction company. He was grateful to me for making his clearances quickly in the past, so he took full control and asked me to just visit the place once it is all over. So again I was left alone with nothing productive to do. I started a youtube channel, where I posted the videos of some of my philanthropic acts to encourage others to do the same. But it wasn’t well received so I discontinued uploading videos although I continued offering donations and foods just for my personal satisfaction. This was the time I came across night life of the city. Which got me back my adventurous I used to be. But I wasn't totally into it. One late evening when I was trying to find people to offer the food I purchased that evening I saw this mid-aged woman sitting on the lawn infront of CMBT, Chennai. She told me it’s 1000/night (but it was actually for 3 hrs). I wasn’t really in for having sex but I felt lonely and asked if she can stay till morning. She said that will cost more. Money wasn’t an issue for me, but just peace of mind so I was willing. And why I chose her to hang around was her ingenuity, and also she seemed reasonable and polite. She had a charisma unexpected from a prostitute. I got to know she was forced into prostitution in Mumbai when she was around 13. Escaped from there and when she couldn’t find any other job to earn good money to take care of her 2 daughters she continued renting her body. I listened to her past patiently and then took her to a restaurant when I got to know she didn’t have her dinner. I gave the food I already had to another old man lying down near the place I parked my car. She was pleasantly surprised by my act. She told me how worse men treated her, and continued narrating many of her bitter past. I just drove mindlessly around listening to her stories. At one point she asked how long it will take to reach my place. That was when I realised I wasn’t going anywhere and then asked for directions to her house. She kept asking “Why” while at the same time obediently giving the directions. She said her daughters don't know about her job. When we reached her place, one of the kids was awake and was studying, occasionally staring at me. I looked around her dingy house and realised how pathetic a life some people live. The woman got me water and said thanks for coming to drop me safely “brother”. She lied her daughter I was the owner of the firm she was working. I then said - okay it’s late, I am leaving, “oh yes here is the increment you asked last month” and handed her a cheque for 5k and proceeded to leave. She was shocked and got tears when she opened. She came running to the entrance and said you are like a god. She hugged my shoulder and swiftly fell on my feet before I could stop. I told the money is for your daughters, do take good care of them and find for yourself a decent job soon. She looked puzzled and said she tried to find but in vain. So I gave her my number and asked her to call me after 4 months and left. I spent the next few weeks just eating, sleeping, porn and gaming. That was also when I met many girls through dating websites and chatting apps, met only few because the rest were just gay men in disguise. But it was hanging around and I didnt like them. My house was ready by then. I shifted to this house renting the one where I stayed. The villa has 2-floors. I rented the 1st floor to working women as PG for additional income only, not for anything sexual, because I don’t mix business with lust. They had a separate entrance from the back of the house hence they didn’t interfere nor do we get to see each other. Because I was interested in horticulture and fisheries I set up garden on the terrace and big tanks in 2nd floor for fishery. But I needed assistance to maintain these hence I needed a woman. I thought of hiring the pros woman for helping me with my garden if she called me but she didn’t. So I hired a woman in the area who was also doing cleaning work for the PG. When I was in Assam I there was this home-borne woman, who was the widowed-sister of my driver. She cooked really well so I brought her here to cook for me. I didn't think she will come but they gladly sent her here. I also needed a maid for my house so hired one from down-TN. She is a widow too with a school dropout daughter. Everything went normal at the beginning. There were 2 small rooms and 1 medium room in the ground floor. The medium room was mine while the cook and maid lived in the other 2 rooms. Because of language barriers these women however cordial, couldn't talk to each other. This was only incidental but later happened to be an advantage. My room and 1 of the 2 small rooms were adjacent while the other room for the maid (with attached bathroom) was opposite to mine and a separate bathroom next to it for the cook. There is a small staircase inside my room that will take me to a big room in the 1st floor which is locked from inside. This is the only room in 1st floor not for PG girls’ access. I got the cook and maids all women because they can do household works without complaining and also can earn extra helping the PG girls. The maid suggested commercialising fishery and hence I allowed them. Both maid and her daughter already had some idea about fish breeding. I helped them commercialise by advertising it in the internet through which they were earning some money. The cook also cooked for the PG girls and it was all settled. I too was doing my own things. Got addicted to games, and at night I moved out roaming and driving aimlessly reaching back home only at dawn and slept during the day. Let me tell you one of my fetishes. I like shemale porn, but only if they look very feminine. Not the ones looking like a cross-dresser we see on the roads, begging. I happened to come across one such trans through a website and she herself asked for a casual meet although she wasn’t a hooker. The meeting was in a mall, a place I detest, I don’t like places that are crowded. We met, spoke for a while and I must tell you she looked nothing like she was born a male. Even her voice was feminine, may be because she had the surgery done? I don’t know. She was dressed in a simple kurthi and looked like any other girl in the mall without any weird makeups and cheap modern dresses you’d expect from a typical shemale. I did ask her some uncomfortable questions but she answered it all very calmly and politely. For instance I asked which toilet she will use and she replied “Any toilet that is working”. “We use toilet to just get our business done right?” with a smile. The conv I had with her further changed my opinion on trans people. She even wanted to pay for the entire food we ordered, but after some discussion we decided to share the bill and she was happy about it. In a way I could sense some feminine as well as masculine gestures. I am a good listener and so I kept listening to her talks by asking many questions. She was shy but she felt comfortable with me. All her small body languages and movements were all what you’d expect from a typical shy girl. My curiosity whether she was really born a male kept increasing the more time I spent with her. We went to a movie but I couldn’t focus much on the screen and secretly kept looking at her. Because it was all a new experience to me I was looking at her like how a new born would. My interest on her now was beyond sexual and I started seeing at her like a girl, observing her actions. If there is a joke in the movie I’ll immediately look at how she laughs and reacts secretly without wanting her know just to capture her natural behaviour. And it was all Really REALLY cute and more feminine than any a biological female. During the intermission she gave cute *sigh* and kept talking with a smiling face about the film. I didn’t really pay attention to what she was saying and kept staring at her lips saying “hmmm..hhmm” “yeah yess”. She realised I wasn’t paying attention and said shall we go get something? I said “yeah sure”. She got up and I too got up catching her wrist and kept holding on to it till we reached the aisle. The queue in the food court was long. As we were waiting silently she turned towards me and said “I never went out like this with any guy for the fear of getting abused”. “You are really being nice to me, thanks for making me comfortable.” I had a relief, I thought I kept asking uncomfortable questions and wanted to smooth it out but this came as a pleasant surprise. I also felt bad imagining how much abuse she should have faced to consider my questions as normal ones. Again I kept looking at her and she too kept talking about many things mostly about her ambitions, future. After the movie got over and as we were walking towards the Entrance of the mall she said it was her birthday and thanked me for making it memorable. I was surprised and went “OMG, why didn’t tell me well before.” She gave a shy smile and was like “it’s okay it’s okay…” and said she wanted to leave quickly because her friends will be waiting in the hostel for the party. Me: “Am I not invited?” She: *smiles*hmmmm it is a female hostel. So… Me: “okay. How will you go from here??” “Can I drop you at your place?” She: “I’ll book a cab”. “Hmm,,, So you want to know where I live?” Me: “not exactly, just to make it easy for you.” She: “okay…. Will you drop me a little bit away so my friends won’t see me? Me: “sure thing”. While driving I was all the time wondering what I can get for her. I really wanted to stop near some stop but that wouldn’t be nice to buy a present taking her along. Her hostel was also not very far so I wasn’t left with any option. As we neared the hostel she said “Stop stop stop.. I’ll get down here”. I held her hand as she was getting ready. Me: “Thanks for spending your birthday evening with me; I don’t know what to present you…. Hmm…. Can I kiss you?” She: “What??”…… “Don’t be crazy!!” “We barely know each other”… “So all these kind gestures just for this?” ME: (felt really bad) “I’m sorry!” “I just … okay I am really sorry” She: “ Fine!” “Look.. mmm…. let me not leave you disappointed”. “Just one kiss on my cheek. Okay?” Me: “wow! Thanks, I really meant a kiss on the cheek only……” “At least come a bit closer if you really meant it.” She smiled, came a bit towards me. But when I was getting closer she moved away and it became like a little game. We got excited and giggled as she continued to fool me. Suddenly I held her face tightly and gave a forceful lip kiss; although she wasn’t giving in. I just kissed her lips for few secs but then she pushed me away breathing heavily and went silent. She then adjusted her dress, hair and said “okay bye, good night” *with a stern face and left.* Actually our entire act was recorded in my dashcam which I only later happened to realise. Next to come is an adventurous sexual encounter. Stay tuned!
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