I went to Chicago for training for two weeks. I happened to be in town for New Years. I started my New Years celebration at the training center. I ate as they cook a meal. I stayed and then headed out on the Chicago metro. I went to a bar called Jackhammer. I did some research online and found out that they had an underwear party. I wore my “gay pride” underwear, they are American Eagle rainbow colored boxer briefs. I started the night off by checking out Jackhammer, it seemed normal enough. I later made my way to The Hole. The Hole is another bar in the basement, where they had relaxed the dress code to shirts off, but you could take more off if you so chose. I went down and the guy told me the clothes check was just round the corner. I went around the corner, there were fat guys, thin guys, buff guys, old, young, sexy, no so sexy, leather, boxers, briefs, jock straps, and nude guys. I thought I was home, lol.
I went to go drop off my coat and shirt, I took both off and started to hand the bag to the thin older guy wearing a leather work belt. He asked if that was all I was taking off. I thought about it for a moment, and said “I said no regrets this time.” I went to the bar and purchased one beer as there was technically a one drink minimum. I had a session the next day and was told I should not show up hung over. I walked around after some time to just admire the scenery. I made my way to the area that was poorly lit and said “Lay Time”. My first thought on the sign was that the “P” was missing. I stopped one guy and asked what this area was, he said it was for guys who are willing to play. I ventured my way in.
As I entered I saw guys having intercourse literally to my right and left. I walked around and saw the sex swing and the pummel horse, that had one guy laying down on his back while no less that three other guys took turns penetrating him. I saw this really cute guy and told him that I liked his undies, he said thanks, and then I asked him what the etiquette was in this situation. He said that you just gently stroke the other guys genitals, and if he isn’t interested he’ll ignore you and if he is he’ll engage. I thought I was going to pass out, this was like a dream scenerario. I ended up having on older biker guy that continuously grabbed for my junk. I kept brushing him off. I ended up blowing the cute guy with the advice, he topped me, I blew a fired of his and then two other guys, a well hung black guy tried to top me but couldn’t get his penis in my anus, I even got in the sex swing for that, three guys blew me, and at the end of the night I jerked off in my boxers which I was holding in my hand while several guys watched. It was a hell of a night.
Well this catches us up for now. It’s been just over two weeks since New Years and that means we are caught up. I have two guys that I’m talking to and a gal that I’m very interested in. Don’t worry I’ll keep you up to date on the happenings to come. Until then Don’t Forget To Be Awesome!