This is a story about the time I had my first anal experience. I was 19 at the time, and had just finished one week long training session where we stayed in bunks, so no jerking off. When we left to go home on Friday, I was extremely horny, having been unable to cum for 6 days. So as I was travelling back home on the bus, I browsed Craigslist. There was an ad for an older gentleman looking for someone to fuck. I've never had great luck on Craigslist, and also been very cautious. But I thought why not, and replied his ad with some pictures of myself as per the ad's request. Within 10 minutes he replied me, loved what he saw and wanted me to come to him, replying with only his face picture. He was a white man. This is commonplace here in Australia but I was in Singapore. When I first saw him, he was huge, like at least 6' 3" maybe more. I met him at his hotel lobby at the bar, and we had a couple of drinks to start. He was from Australia, but I had forgotten which state he was from. He was in Singapore for some business and wanted to fuck someone. I asked him if he was alone, and he said he was but he has a wife and kids back home. I asked him how old he was and he said he was 52. So anyways, we finish up our drinks and headed up to his hotel room. We continued chatting as we walked towards his room. To my amazement he had gotten one of the luxury suites in the hotel. And it was massive. He had a king single, a sitting area as well as a bathroom with an open window to the bed. He asked me if I wanted any more drinks, and I accepted. We started walking towards the massive bed and proceeded to undress each other. I unbuttoned his shirt and he pulled of my t-shirt. Then he unbuckled my belt and pulled my jeans off me. I proceeded to remove his belt and business pants. I could feel his bulge as I was pulling his pants down. Then, we were in our underwear, our dicks very visible and our bulges waiting to burst out of their fabric cages. He put his bearded face close to my crotch, so close that I could feel his hot breath through the fabric, but not touching. Then he grabbed the sides of my underwear and yanked it down straight to my ankles. He did it with such verocity that my semi-hard erection smacked him in the face. He laughed and said "Better be careful there bud, you might take an eye out!" I did the same for him, and be was soft but huge. I was probably 7.5" but he was slightly longer at probably 8" and slightly thicker than me. I reached out and weighed it with my palm and it was hefty. I could tell he was aroused as it started to get nice and hard in my hand. I was starting to get nervous... I told him I had only had dildos in my ass but nothing as big as he was. He was very patient, teasing my cock, taking both our cocks and rubbing it together. I felt the heat and his throbbing cock on mine. We skipped the oral because it wasn't something he was interested in, so he got the lube, squuezed some on his finger and teased my asshole. He told me to relax and push out, and this seemed to work as he managed to work a finger in. He got more lube and managed to fit 2 in there. I couldn't wait anymore and told him I wanted him inside of me. He slipped on a condom, which could barely contain him, and layed on his back. I decided to slowly ease myself into his huge cock. Slowly back and forth, and he was patient. Finally as I was halfway down his shaft, I felt myself finally loosen up and I slid down all the way, taking all 8 inches inside of me. And I slid down onto his rod, my cock was just oozing a steady stream of pre-cum that landed on his belly and glistened. He seemed to think it was sexy. Finally I could take him all in. I had never felt so full ever in my entire life. And so I began, riding him slowly, working my way up and down, all 8 inches of this stallion. I looked down and saw my cock was bigger than ever, and hard as a rock. I didn't know my dick could get so big. I began to ride him faster, my hard cock slapping his stomach every time I came down. The contrast of a brown dick on a white man was such a turn on. Finally we decided to switch positions, and I assumed the doggy style position. Face down, ass up he grabbed my hips and entered me once again and I let out the loudest moan ever. I just couldn't help myself. I kept backing up onto him following his rhythm. He cries out "Fuck you're so tight! I love it!" And the slaps my ass. We continue this for a while and then he said he was getting close. So I layed on my back, he grabbed my legs and made me hold them in the air. And then slammed his cock back into my boy pussy. I let out a nice stream of pre-cum that pooled onto my stomach. He pumped away, with my legs in the air, and used my dick as leverage to pull himself closer into me. Then he said he was about to come. He pulled out his dick and ripped the condom off and showered me with his hot load. It was like a geyser, he just kept shooting his load all over my hairy chest and stomach. And then at that same time I came and my load shot up in the air, and landed on my chest and neck. He proceeded to rub all of our cum all over my body and nipples and stomach. I was exhausted and he was as well! And he was grinning so much. I told him I had made such a mess and has to clean myself up, he suggested taking a shower together. As I got off the bed, I realised I couldn't walk straight, like a baby deer. I eventually found my footing, and made my way to the shower. We both got wet under the shower and proceeded to soap each other up. Eventually we got cleaned up and we sat down and had a chat. He asked me what I wanted to do in life, what I wanted to experience, and gave me some life advice. I thanked him and left after that. Haven't seen him since. But that was one of the best fucks I've ever had in my life. Part of me think that it was his dick that made me move to Australia.