After completing my second year of college, a couple of friends and I decided to get a hotel room and party. They were guys that I occasionally fucked around with when I visited the city on weekends. Craig was a black, chubby guy who was versatile and Stan was a top black chub who was an offensive lineman for a local semi-pro football time. We’d meet periodically and have a 3-some with Stan being the alpha and always taking the lead. It was also a time in which I drank heavily and discovered how much it lowered my inhibitions, which is good and bad.
We played “truth or dare” with shots involved and the more it went on, the drunker we got and the more adventurous it became. Craig dared me to go outside and bring a homeless guy up to the room to blow him. After an outright refusal from me, I eventually broke down and decided to do it. It was extremely hot outside so my hope was that the homeless guy could be talked into coming for a few beers and the air conditioning.
I went outside and noticed he was talking to a couple of other guys, so I waited to hope I could get him alone. Soon my window of opportunity opened. As he sat alone on a bench, I joined him and started some small talk. He introduced himself as Earl and was very friendly. When I offered to join me and some friend for a cold beer, he gladly accepted. Probably recognizing him, I got a few strange stares from the hotel personnel in the lobby but no one said anything.
Once in the room I introduced him to my buddies and we sat around drinking some more, but the topic of sex hadn’t come up yet. Earl, Stan and Craig were getting along very well, lots of laughter and stories but I was more focused on how I would get him to let me suck his dick and was unable to enjoy the conversation.
Finally, Stan brought up the topic. “James, don’t you have a request to make?” he asked, looking at my slyly.
I wasn’t ready to respond to the question and remained silent. So Stan took over, as he usually does. “My buddy,” Stan said as he got up and placed his large hand on Earl’s shoulder. “James here has a real skill that he wants to try on you.”