My Life As A Gigolo In Chennai – Part 1

Hey ISS readers, this is Rajesh from chennai ([email protected]) back with an real life experience. And thanks for the overwhelming response for my previous story https://www.indiansexstories2.net/couple/sex-in-the-college-playground-with-shruthi/

So once I graduated from college I joined a mundane 9to 5 job at an it company here in chennai. And I had an a breakup with my girlfriend shruthi whom I mentioned in earlier story . Being lonely was taking a toll on me and I was kinda bored. That’s when I met a person called sathish who happens to be my new neighbor .As a matter of we hit a bar in a week and eventually start speaking about our lives and other stuffs. In the due course I was saying my lonely and boring evenings ,that’s when asked me this straight question “how good are you in handling a woman in bed ?”. I was stunned by his question because I barely know this guy for a week and he shoots me a intimate question.

I somehow controlled my rage and said im good at handling women (i have fucked my gf’s and been with lot of call girls in the past !!) .He smiled at me and said then you have a bright future and said that he is a independent gigolo and asked me whether you would like to join my network . I was speechless because obviously I knew what gigolo is and I was quite skeptical in taking that job . He sensed my tension and said gigolo is not just about fucking a woman . It is more of companionship ,you need to go out for a movie or dinner or even just talk to them bcoz the women are lonely out there.

This proposal somehow got me excited and the next day I called up satish and said I am up for the job . He came back in the evening with a beer and he started explaining what a women will expect from a male companion and this job is all about pleasing her and not about you. He explained a lot on professionalism and so on. And he told me from now on I will handle the small time customers since he is handling women of higher stature . Sathish gave my first assignment ” kalpana (name change)”, the woman is a widow of age 36 and he just gave her number and a address in T.Nagar. I need to visit her the next day afternoon . And obviously I was nervous because this is the first time as a gigolo.

I texted to her mobile and asked her to call when she is free. Kalpana called me in the evening around 7 pm and I just gave her a friendly talk and I gathered that she worked in a it company as a project manager and got to know about her basic likings.

The d day came in and I grabbed a set of condoms and dressed in a very casual jean and t shirt. And about me , i’m a average looking guy with a 6.5inch tool unlike others in iss who have a 10″ or 13″ tool. I met her at cafe coffee day in t nagar.Actually I reached earlier and I was waiting for her .There came a not so beautiful but yet attractive fully grown woman entering the shop. She identified me and sat just opposite to me. That’s when I had a good look of her.

She had a whitish skin and awesome structure and had a flat tummy. She was wearing a black saree in contrast with her skin complexion ,she was literally glowing in that attire. The makeup was light and was just making her look even more sexy .She had freed her hair and in a instant any one looking at us will think we are couple because she looked that young. We ordered a cup of frappe and a cappuccino .

She was bit tense and so I broke the ice by starting a conversation. I said about my personal likings and she said her husband passed away in a heart attack long back and she was all alone. All this time I was advancing with my toe by slowly massaging her toe and she started to like it and just blushed at me . Soon we just drove to sathyam cinemas and bought a corner seat ticket for a sick tamil movie.

Since it was a afternoon show in a working day there was a very little people in the theatre. She was simply talking on various stuff , as the movie started I slowly started to put on hand on her shoulder and with other one I was massaging her thigh which was so smooth over the saree. She was ultimately and aroused and stunned because of my behavior in public. This ignited a passion between us that I forgot everything around us and I stared playing with her boobs. Even over her silky blouse and a tight bra they felt so soft and so good .She started to massage my tool over my jeans. She was too irresistible that I kissed her on her lip.

At first she did not respond well and she slowly opened her mouth and our tongues played the battle, we had a passionate kiss and that’s when we decided to leave the cinema and move to her house. Those 30 minutes of driving was the longest 30min for me in my life. While driving I was just massaging her thighs all the way and I occasionally groped her fully grown boobs . We reached her apartment in T.Nagar.

We both were so excited that once we got in to the house we started to kiss and this one was a real passionate one slowly brought my hands to her boos to get a firm hold of it and I started to fondle it then I slowly moved down kissed her neck and as I sucked licked every inch of her neck and her back we moved to her lavish master bedroom and I just pushed her to the bed. I removed her pallu or saree till her waist . You know at that point she looked like a sex goddess to me in just a blouse. I kissed her inner part of the blouse and her beautiful cleavage and I removed her blouse and bra very slowly that I can capture the whole moment for her . Her stats was 34d-32-36 and her boobs were fully ripe and though a little bit shaggy but was firm enough for a 36 year old women .

I started to vigorously lick and suck her boobs simultaneously , even I left a love bite as souvenir .She was completely sweating even though we were in ac room which was filled with her moaning sound and my slurping sound. That’s when I got an idea and took a bottle of honey form her kitchen just poured it over her boobs and started eat the honey. Kalpana was too aroused she even had and orgasm out of it . I slowly moved down to her naval and started liking it

To be continued …….

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My Life As A Gigolo In Chennai – Part 1