Started with an IM and now we're here

I’ve always messed around with guys coming up. I identified as straight but, every now and then I got down with a dude. Since HS, when my homeboy’s younger brother turned me out. It was more of him going down on me and that was the end of it. It wasn’t til I got to DC where I branched out and did more. I have stories but for now, let’s move on.

Fast forward to July of 2000 and I’m in NYC messing around on Blackplanet. I was in the gay room and I happen to mention that I had a birthday and wanted a gift. Nobody really responded outside of “Happy early birthday homie and I hope u get it.” I then get a message from a guy who lived in Manhattan asking if I was serious. At first I was gonna say no but, something inside me told me to respond yes. So he told me to meet him at work in a few hours. I get showered up and I’m off to Manhattan. I get to the address but, I’m afraid to go up because there’s a big ass dog growling at me. He then comes down and he is AMAZING. Think of an older (cleaner) DMX. We puts the dog up and we go up to the top of the building where his office was. We have a few drinks (he owned the company) and then go up the roof to look at Manhattan. After some more small talk, he leads me to his storage room where he gives me amazing head. As he goes down he works his finger into lube and enters my ass, he then gets me close and he sits me down on his cock.

Lesson here folks is to make sure you look at the size before u jump on it. Especially if you haven’t been penetrated in a few years.

I jump up in pain but, he assures me the worst is over so he bends me over a couch and slowly eases himself in. When he gets inside halfway, he picks up his pace and WOW!. He starts fucking my ass really hard. The pain was immediate but, as he continued to stroke and I got used to the size, I start to throw the ass back at him. He kept on whispering how he loves the shape of my ass and how wet it was. At this point he didn’t need more lube because I was so wet. He told me how that ass belong to him and I readily agreed. I looked up and I saw his friend staring at me. The guy then flips me over and re-enters me in a missionary position. I was in so much pleasure I didn’t even touch myself, just lay there and work my hips. He starts to jerk me and I came in a matter of minutes. He then licks his fingers clean and wipes my cum over my stomach and at that moment, I feel him shoot inside of me. As he pumped he grunted that his cum only belong inside my ass and continued to pump until he was completely drained. I laughed as his friend cheered the show and got up to get dressed. As I sat on the train, I felt his cum ooze out (thank god, I wore jeans). He hit me up later to invite me to a party that weekend. I wasn’t able too and I lost contact with him. But, I credit him with opening me up to a new world of possibilities. Wish I could find him again so I can show him what else I learned….

Until next time…