Young/Old Hotel Room Fun

This is a true account of how I lost my anal virginity. It was one of my first gay experiences, and it happened just after I'd turned 18. More of my sexual adventures will be uploaded if this one is well recieved.

A few weeks after my first gay experience, with a guy my own age, I was horny and wanted more. Since I've always found older men to be a huge turn on, I decided to search the internet for some fun. Sure enough, one of the first ads I found on a local online craigslist-type website was for someone looking for a younger guy. "Mature well built older man seeks young students/legal age schoolboys for discrete fun. Can host in safe secure venue."

I sent him an email, and waited with a mixture of excitement and fear for a reply. It wasn't long before I got one, and we had arranged to meet at an upmarket hotel. As I walked up the stairs to his room, I felt my heart beating in my chest. I was nervous, but horny and excited enough not to chicken out. I knocked on the door, and he opened it immediately.

He was slightly older than my ideal man, probably in his fifties or sixties with gray hair. He did, however, have a nice strong build and was quite tall, like a rugby player. He invited me in, and we made small talk as we had a drink. I was really nervous and shy, as I had never done this before. Finally, he cam close and put his arms around me. Immediately I got hard, and pressed up against him as I slid my hand down his pants and straight to his semi-rigid cock. It was a strange feeling to be touching another man who was so much older than me, but this just made it more of a turn on.

He pulled away long enough to quickly take off all his clothes, and I took the opportunity to do the same and then lie down on my back on the bed. He wasted no time in putting his head between my legs and sucking my balls as he slowly jacked my by now rock hard cock. Slowly, he made his way up my shaft, licking and sucking as I arched my back in pleasure. He pulled my foreskin back and finally took my cock in his mouth properly, and sucked hard as he bobbed his head up and down.

After blowing me for a while I asked him to stop, as I was about to cum and wasn't ready for and end to this naughty pleasure. Without stopping, he moved down past my balls, towards my virgin asshole. I instinctively lifted my knees towards my chest, giving him full access to my tight clean teenage hole. He licked it hard, before slipping in two fingers, which he'd smothered in lube. His fingers felt kind of pokey, so I pulled him up on top of me. We kissed, and I felt his tongue firmly probing my mouth. I still had my legs up and open, and could feel his dick rubbing around my hole. I hadn't planned on being fucked today exactly, but I was definitely open to the possibility.

So when he slipped a condom onto his dick and lubed me up some more, I lay back and let him do it. He pressed his dick into my asshole, but I has too tight to take him immediately. After some more lube, he pushed in again, and this time his entire cock slipped in. A burning pain filled my ass. I let him keep it inside me for about ten seconds, but the pain did not subside so I made him pull out, promising myself to try this again soon.

By this time we were both extremely horny, and about to cum. he lay on his back next to me, and I wanked his cock until his entire body jerked again and again as thick streams of cum flew out onto his chest. Then it was my turn. I kneeled on the bed and pressed him up behind me, guiding his strong manly hands around to my young cock, which stood straight up, ready to explode. After just a few tugs I felt a massive orgasm wash over me, and I spurted repeatedly onto the hotel bed.

After that my arousal subsided quickly, and I showered, put on my clothes and left as quickly as I could. Although I felt somewhat ashamed and dirty to have had sex with such an older man, I knew it wouldn't be long until I would go looking for more cock. And sure enough, it wasn't. But that is another story, for another day.