The Beginning Of Being A Gigolo

Hello. I am back with a story after a while. I am 24 now, 6 ft tall, a little chubby with 5-inch dick. I study and work as a freelancer. This is a fictional story and not real.

I moved to a new city after completing studies. With no financial support from my parents, it was hard to start with. Finding a place to live in and getting 3 square meals every day was turning out to be difficult. Moreover, I did not have a job yet.

I used to wander the streets of a strange city with a resume in my hand looking for a job. Finally, I found a job but it was a hell of a surprise for me. One day, in my daily endeavor, I came across a sign that said young men wanted. I got so excited that I did not read the rest of the sign.

I went in and was handed a form where I filled in my details. Then there was a test that followed, which I thought might be a standard medical. However, they were way too interested in my dick and sexual health. Desperate for a job, I answered all their queries to their satisfaction and they said I should wait for their call.

In a few days, I got a call from them and everything became clear to me. They wanted me to go to a gated society, and spend some time with a middle-aged woman for which I would be paid. I was apparently a member of some friendship club. I was in a moral dilemma.

I did not want to be a gigolo but then I needed the money desperately. Finally, I decided to dress up and check it out. After all, it was a strange city where no one knows me and I have nothing to lose. It was a posh society, with 5-6 towers each 20-25 floors high.

I had the address where I needed to go to. My name was already on the visitor’s book and I was guided by the security to the building. The woman who opened the gate was in her mid-40s. She was wearing a top and jeans. I was really nervous, slightly sweaty. She ushered me in and asked me to sit on the sofa.

She handed me an envelope which I hoped had money. It was a thick envelope which made me happy. We had a little small talk and she asked me if it was my first time. I said yes. She smiled and got us some beer. Alcohol always opens me up and with every sip, I grew less nervous and hornier.

I started checking her out as she sat next to me on the sofa. She had medium sized perky boobs and around nice ass, not too big. She was maybe 5’2” and slim, wheatish complexion. I was horny enough to start getting an erection. I moved in closer to her and by the end of the bottle I was making out with her.

I sucked on her lips, holding the back of her head. She had a sweet lip balm on which made it really enjoyable. I kept biting her lips as my hands started exploring her curves. I moved my hand from her head to her neck, down her shoulder and cleavage to her crotch.

She parted her legs with my slightest touch and I started rubbing over the jeans. It was getting too heated for the sofa so I moved to the bed in the next room. I could feel her squirm a little as I kept making out and rubbing her. I started undressing her, and there was not much to undress.

She was not wearing any underwear. I took her top off and started rolling my tongue around her nipples in a circle as I took off her pants. She was hairy but I did not mind. As I slipped her jeans off I started nibbling on her nipples. My mouth worked on her boobs as my fingers slipped into her pussy.

She was wet and warm which made me harder in my pants. I sucked on her boobs as my fingers slipped in and out of her and my thumb worked on her clit. She was moaning lightly and holding my hair in her hands pressing my face into her boobs. I traced a line with the tip of my tongue from her boobs, down her navel to her pussy before I started eating her.

I held her legs apart and teased her thighs a little, kissing them and licking them before I started licking her. I kept her pinned down to the bed as I ate her out. She tasted salty and thick, warm and wet. I licked her clit, sucking on it hard before I pushed my tongue in her.

I could see her squirm and hold my head down on her pussy. I kept licking her, sucking her clit and moving my tongue in circles inside her till she came right on my face. She was a timid kind, so I had to do most of it. I slipped out of my pants, put on a condom and started grinding against her pussy as I squeezed her boobs hard.

They fit perfectly in my palm. She was turned on enough. I started moving in slowly inside of her. She was tight but I couldn’t come so easy. I started slow, rubbing hard and deep. I could see her back arch as I started fucking her harder. She came twice in under 20 minutes and I came inside her.

She was the timid kind so I guessed we should cuddle for a while. I went in and left in under an hour, fucked a woman without even exchanging names and I was 20000 richer. I loved my new job.

Let me know how you liked my story at [email protected] and I will share my other fantasy experiences as a gigolo in the stories to come.