My first time was the result of a long building desire to have sex with another man. It was also the result of my girlfriend of three years.
To start out, myself and Shea had been together pretty much since I was 17 years old and she was 15. I was 21 at the time, and I was going to a wedding of a family friend I had known for a while. Now for the backstory. Shea was pretty straight laced, she didn't like being freaky like I did. The wedding was in July, and we had been having some troubles previous to this. Right after Christmas, she got mad and we broke up. My desire for all things anal had become an issue. When we broke up during Christmas, I went out and bought a dildo. It was the first one i had ever had, and I used it non-stop for the week we were apart. Shea found out, and she was hurt, but I was in love with her and I agreed to be with her and not the dildo. We made it okay until May, when things hit the wall and fell apart. Shea basically informed me that we were done. I tried as much as I could to get her back, but to no avail. About the same time, I had a friend who came out of the closet, one whom everyone knew was gay. He came out to my close friend, and then told everyone that he had a boyfriend, whom everyone called Chocolate Thunder. It's exactlly how it sounds.
Now, I had a picture of myself using my dildo on my computer, and to make a long story short, my newly gay friend found it, and tried to blackmail me into having sex with him. I turned him down, and informed Shea of what he wanted. That is when she started accusing me of sleeping with him. She always told me that when I had sex with him, I needed to use a condom. I laughed it off, but it was pissing me off a little. Now to the wedding.
I went to the wedding, and my gay friend and Thunder were both there. They had a hotel room and were ready to party all night, which they informed me of right away. I laughed it off, and kept drinking. I thought of Shea and how much I loved her. And I got drunker and drunker. Soon, I was handed a room key to the "party" room. They then left and went up for an ass-fucking bash. At this time I went up to take the room key to them.