My First Time

I have always been a chubby guy. Even as a kid, I was always flabby and in a world that idolizes muscles, it was disheartening to experience contempt from my friends due to my flab. And if my weight wasn't a problem, the fact that I was a gay teenager from a rural part of India certainly didn't make it any easier. I didn't know any gay person in and around me and when everyone was experiencing their "first", I was still jerking off to Google image searches (I didn't discover the better side of the internet till I was 16).

But one day, my first year of college no less, I discovered the world of online dating. I am not sure now about how I found it but it certainly was a revelation to learn there were so many gay people in my town and neighbourhood areas. Of course, I didn't know anyone by their personal information but just the idea of being surrounded by so many gay and bisexual men, made my teenager dick go on overdrive. I spent hours online, searching for someone, talking to strangers, but it never went anywhere beyond that.

See, I didn't just want some random dude for my first time. I wanted a daddy bear.

And, then, I found him. Or rather, he found me.

His profile name was TilakXXX. His description gave the idea of a 40 year old, chubby, hairy dude who wanted a chubby bottom. When he came across my profile, he was hooked by the fact that I was a chub too. He and I spoke for days, realising that we are looking for someone exactly like the other. Soon, a day was fixed to meet up.

He gave me his address and asked me to come on a Saturday morning when his family would be out of town. I made my way to his beautiful suburban house in the fringes of our town and stood in front of his door, scared to knock. The teenager in me was raging to walk in, grab this hunky daddy and go to town on him but my brain kept going, what if he's a freak or a psycho.

Well, obviously the teenager in me won because I did knock on the door and in a few short moments, the door opened. To say that he was hot would be an understatement. He wasn't the best in looks but he sure did seem hairy and a tight beer gut hung low, proud and strong. He invited me, offered me a soda and we started making small talk.

While talking, his hand was rubbing my thighs, almost touching my penis but not quite. I took that as a cue and started doing the same, but I went straight for his goods, rubbing them through his pants, fondling what seemed like a thick cock and rather large balls. He sighed in approval and leaned in for a kiss, my first kiss. At that moment, my body erupted in metaphorical flames as I got tongued in my mouth for the first time. It was a wet sloppy kiss that soon gave way to him quickly taking off my shirt.

"I love a guy with boobs", he said as he pinched my nipples. That was the first time I realized hoe erogenous nipples could be and I came close to creaming my pants. He took off his own shirt, and pushed me on my back and laid down on top of me, kissing me and playing with my body like it was putty. I couldn't help but run my hands through his very hairy body and back, rubbing his back muscles, squeezing his love handles and moaning like a Japanese porn star. He whispered in my ear, "let's take this to the bedroom", and off we went.

Inside the room, he took off his pants and asked me to do the same. I was very shy so I kept my dick covered with my hands and he, on sensing my hesitation, came close to kiss me and grabbed my hands, pulling them apart. He pushed me to the bed and laid down next to me and was fondling my penis while I rubbed his. But, I was done with the foreplay, and so was he. I slid down his length, kissing his nipples, running my tongue through his stomach hair until I came face to face with his cock. He wasn't the biggest guy I had seen and neither was he the biggest I have taken since, but at that point, he was adequate enough for me. I remembered all the images I had seen of people sucking and dove straight in, sucking him like a vacuum cleaner. He laughed at my inexperience and asked me to start slow, to lick his cock first and to take my time, lest I tire myself out. So I went slowly, licking that prime piece of dad meat, smelling and relishing that leathery texture and that musky smell. When I got tired and my jaw hurt a little, I slipped down and took his balls in my mouth. I was surprised by how great they feel, rolling inside your mouth, like a small candy with its wrapper on. All this while, my daddy top was breathing deep and making beautiful moans but that was to end. He was ready for the main event.

He told me to slide up as he slipped down. He made me get in a doggy position as he started licking my ass and oh my, what a feeling that was. I had no idea how incredible a tongue feels in the ass and copious amounts of my precum slid out of my cock as I desperately craved for an orgasmic relief. Suddenly the tongue was gone, followed by something thin trying to enter my asshole. At first I was a bit confused but on looking behind, I saw him smiling as he started sliding a lubed up finger inside me. The sudden intrusion inside was painful as I winced and tried to move away. But he had anticipated that as he grabbed my shoulder and kept me in place. He told me to relax and that the pain would pass in a while. While it seemed like a long time, I realized the pain was gone followed by a feeling that, while not entirely pleasurable, was nice. As his finger slid in deeper< I experienced the first joy of fingering as I moaned in the unexpected pleasure of, what I assume, was my prostrate getting tickled. Like a kid in a candy store, I wanted more so I thrust my ass back to take his finger in and he took that as a cue to slip a second finger in. He continued fingering me for 10 more minutes by which point, I was begging him to stick his penis inside of me.

While we had decided to not fuck bareback, he asked me if I would be willing to try it. And I was so worked up, I would have said to just about anything he said, so I told him that I would prefer being barebacked. He lubed my ass one more time, covered his dick in lube and lined it to my asshole. While I had been fingered so the initial pain was considerably less, it was still quite the ordeal as my asshole burned from his intrusion and I started to cry. He pushed me down on the bed face-down, laid on top of me and started kissing my neck. Slowly, he pushed his entire length inside me as I persevered and took it all in. I was relieved that it had gone all in but that pleasure was short lived as he yanked his penis out of me. Before I had a chance to know what happened, he pushed it back, in one slow motion and I moaned, louder than ever before. He slowly started thrusting in and out, while he pulled me back in a doggy position. His pace quickened soon enough and before I knew it, he grabbed my sides and flipped me on my back, grabbed my ankles to push my legs apart and pressed himself inside me. As I watched his face sweat and concoct in the pleasure of penetrating, I ran my hands through his sweat covered chest and stomach and enjoyed my first. As his thrusts increased, he grabbed my dick in one hand and started stroking me and the combined pleasure of getting fucked and the hand action made me cum, what had to be the hardest orgasm I have had till that point in my life. As I withered and shook in the wake of my orgasm, he started going full throttle on my ass, and bit my neck as he announced he was cumming too. He collapsed in my arms right after and we both couldn't stop smiling.

Before I left his place, we did it again and did it every now and again until I moved away from the city.