Hey all. I have been jerking off to ISS since the last 4 years, and I had only read experiences of male gigolo’s until I actually had a bold chance to have my own experience. Thank you ISS, for giving me the confidence to try and make it happen.
I am a 22 year old guy, and this is an experience which has happened about one and a half years back. I had posted on Craigslist and had done a lot of research before I made a post to see try and get a response. I had absolutely no hope of getting a response, and for a week, i didn’t get any response.
Suddenly, my mail popped about a woman, who was aged 33 at the time, living in Anna Nagar area. Now, I was obviously a little scared on how to proceed further, being my first time and all. So I replied back giving assurity of safety, as that is what will give her the trust and belief that she can chat with me further. And also, I made sure I asked, and she said she is south indian, which I was happy about as it helped me to know that possibility of knowing is less, as I know North Indian community in Chennai very well.
We started mailing back and forth, and they would usually be at least 5-6 lines. It was amazing how we wouldn’t just talk about sex, but anything under the sun. Finally, my patience and my excitement were reaching its pinnacle and I asked for a meet, and this was without exchanging a single photo, as we wanted there to be a connection before we go further.
We chose to meet in an odd area, like Porur, so that we are far from known people, and mostly surrounded by unknown. We had decided the date, and said what colour clothes we will be wearing. I got scared, and I wore different colour clothes, but she came in the pink salwar she said she will in. I went upto her, after seeing that she looks decent, but had great assets, and asked her by her email id. It was her, but she doubted seeing my clothes. I showed her the emails and she then trusted, and we were more glad about the fact that we didn’t know each other.
While talking, my foot touched her accidentally, and then she herself moved her foot on me. Then, suddenly, she said lets go to her house as no one is there. Me and my dick, both jumped, and we went in auto, as we didn’t want to reveal each others vehicle. We were off for her house, and in excitement were also holding each others hands and i had my hand over her shoulder with her leaning on me. There was this odd smile which was also nervous.
As soon as we entered her house, she first made sure to lock the door. While she was locking the door, I went and held her arms from the back, and I pressed my body against hers, and she could feel the hardness of my dick as she closed her eyes in anticipation. I then turned her around, and as though newly married couples, we looked into each others eyes, smiled, and hugged each other really tight.
We could totally feel the connection that was there between us, and we came out of our hug, and slowly went in for our kiss, with my hands around her back. I loved how slowly and steadily the kiss started, and eventually was getting into see who was getting deeper into whose mouth. It was like a competition that was making us hornier. And while I was kissing her, I put my left hand to good use by giving a spank to her ass, and then grabbing it. Her eyes opened but her lips never left my lips and we got back to our kissing with me grabbing her ass tightly.
Now the clothes were coming in between, and hence, we moved into the room, and also decided to get rid of every piece of clothing, and I made sure I kept the condoms at a hands distance away. Then, I laid her on the bed, and got on all fours, with her underneath. We started kissing again, and I slowly slid down to her boobs, oh those incredible boobs. I love boobs in any contour, and hence, I had to go straight fro the nipple. As I began my excavation of her mountains, she let out a moan, which was inspiring me to go at them even harder.
From her heavenly boobs, i moved down to her navel, and eventually, that led to her pussy. Oh that glistening juice maker. It was right there. I blew some wind from my mouth onto the pussy, and she raised her head and asked me to get into it now. I didn’t need her signal, but after that, I immediately reached for the condoms, and started to get into her deep. Oh man, her cunt must’ve become so easy to plunge because of all these years of fucking, and was I glad.
I pumped into her deeep. Pumped hard once. Then again. And then again. And then again until I heard a moan that was loud enough for me. then i positioned myself, and started ramming her pussy, in a way I had never experienced before. Oh man! I tell you, the sound of beautiful fucking combined with the moans of a woman are just incomparable. As she went Oooooooh and Aaah and Fuuuucckk me, I kept going for at least 5 mins, before I disposed by semen into the plastic bags. It was an amazing feeling to be inside a woman, ejaculate, and not have to worry about it.
Thus ended our first romp. The second session was with her on top. I tell you friends, a woman on top is like a queen riding a horse. Magical!
If you liked my experience with the lady, do let me know – – and encourage me to post more of my experiences.
North Indian Boy Lucky In Chennai
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