The Cliched “My First Time Story”

My name is Ashwin, ever since I was a kid, I used to like how girls got to dress up, have long hair, and get make up, and I always wanted that. But those feeling went away as i came to high school, became an athlete and looked quite manly by the time I was ready for college.

Even through all these years though I had that desire in me, and when I used to chat online for sex at such sites, then due to the lack of girls, i would act as a girl and chat with men and women. Soon I used to act as a bisexual guy, on these sites.

When I was in colleges first year, I got the courage to get a new sim and used it to call and talk with other gay guys. I wanted to meet someone, but nothing could get fixed because I live in a small town.

So eventually one day a guy from the next city called me and we talked, and I told him I was a virgin, when it came to men, and he liked that. He was older than me, around early 30s. And I wanted an older man (still do), since I believed he would have experience. So we finally decided to meet one day, he said, he would come to my town, we could meet each other, and if we agree we could do something more…

So I was really excited about it a day before our meet, I was reading blogs about how to do what and stuff.

And on the day of the meet I was at a friends house and we were talking and suddenly this guy calls me and asks me to come to a nearby place and I go there, since we hadnt seen each other we were describing ourselves on the phone while trying to locate each other. I got him first, and I saw him smoking( at that time, I didnt smoke ever), and I was a bit turned off.

But I went to him, he shook my hand and greeted me, we talked, he was manly for sure and was soft spoken as well. That was an agreeing point. We were both on our two wheelers, and I told him that there is a small lodge near a place, and they usually rent it to travelers and stuff. So we went there, he gave his ID and asked for a room since we wanted to “freshen up”.

We got a room, alone in the room now.

For the first time I was a bit scared, i went to the washroom, and relieved myself, tried to not pussy out. I came out, and he was sitting on the bed getting comfortable, and asked me to come sit, i sat next to him. His hands were on my shoulder, and he was gently touching me while talking about stuff. I couldnt keep my mind straight. He then gently drifted his hand over my crotch and started caressing. i was getting harder by his touch, then his other hand was on my shirt, unbuttoning it.

As a knee jerk reaction, I put my hand on his crotch and rubbing him too. He asked me to relax, and leaned forward and started to kiss me. He had a stubble and it kept poking me, but he kept kissing me passionately and then held me tight and kissed me more while fnishing to take off my shirt. I tried to unzip him, but by then he had unbuttoned and unzipped my jeans quite easily. he asked me to relax again and helped me out of my jeans and then himself; I was standing in my undies in front of a man in the same way.

He pulled me close and kissed me again as i stroked his hard cock over his inder wear. he reached down and got inside and held my dick, I was very excited so i asked him to not touch me there and i started stroking him now. He was hard as any man could be.

I kept stroking him as we kissed and then he started to guide me down, and I wasnt ready for it :p I anyway went down, and he pulled away his undies and then out sprang his huge hard cock, I leaned forward and licked the head and his fingers went to my hair, i slowly licked his entire head and then tightened my lips around his shaft, and he couldnt resist, slowly guiding me deeper, i tried to go on till I gagged easily.

I wasnt ready for this either, but I went ahead, slowly licking his shaft and sucking on the head as he guided me deeper and deeper, and my mouth was all sloppy with his precum and my saliva. he smiled at me and started face fucking me slowly, and then increasing his pace.

I was super horny and i looked up at him and said, “fuck me please”, He naughtily asked me again “what did you just say”, I replied “please fuck me hard”.

I regretted that the next second, as i got into doggy pose, he came up behind me and slowly pushed his huge head onto my tight pucker. I moaned and almost shrieked out in pain and moved away from him as i tried not to scream.

He slowly guided me back to suck his condom covered cock now, as I did and tasted a condom for the first time (not my last time though). Then again he laid down and asked me to get on top of him. I slowly placed my legs on either side and slowly poisitioned myself on him, and i tried to open up and take him in.

This time he started to go in and I tried not to clench, as this felt good.

A few more slowl strokes, and I was ready to take him deeper, and I looked at him and told him the same, and he started to raise his hips and started to fuck me harder and faster now. I moaned and enjoyed every stroke of his. We got changed into missionary and he fucked me hard again and kept kissing me in between.

After 2 more poses, we reached back to Doggy style again, and I got into pose, and he asked me to relax and open up, I did and so he entered deep, and i clenched tight and couldnt move as he held me. He started to fuck me hard and deep as he could, I was moaning slowly rubbing my cock as well.

After a significant fucking, I came all over the bed, he pulled out, and came over the ground. I lied there and then went to the washroom. Never met him again

Did you guys my sex story find it interesting. comment and tell me if you did, and I shall write more..