I once was on a business trip in Chicago. In my hotel one night, I was super horny and cruzing online and started chatting with a guy who lived downtown near me.
He told me to cum over because I told him I needed to suck a cock sooooo badly tonight. He had a place in a high rise and when we got down to business he opened his drapes and the whole wall was like glass from floor to ceiling and overlooked the city. He told me let’s do it here so the whole city can see you on your knees sucking my cock!
Best background ever giving a guy head!
I had completely forgotten about this trip to Chicago. My best friend, Jeff, and I had gone to Chicago to celebrate his birthday. My boyfriend stayed home and Jeff was single at the time. Before we went out, we had a few drinks and decided to stuff our underwear. We each put a pair of socks in our underwear, stuffing the pouch. We worked on them for a few minutes, making them look realistic but over-sized.
We walked down to Boystown, and headed to SideTrax. The bar was packed, we were having a good time. Eventually, I noticed I was being cruised by an older, very good-looking guy, Greg. We kept staring at each other, but eventually, Greg came over to where Jeff and I were standing. We chatted for a few minutes when Jeff said he wanted to head back to the hotel because he wasn't feeling well. I offered to walk him back, but he told me to have a good time.
After we had a few drinks, Greg and I walked back to my hotel, so I could check on Jeff. When we got to the room, Jeff was watching TV. He said he got sick when he got back to the room, but he was fine now. I went to go take a piss when I remembered the socks in my underwear. I pulled the socks out before I left the bathroom.
Greg and I went to his hotel, which was near Michigan Avenue. During the cab ride, Greg told me where he was from and that he was in town for a travel agent's convention. We got to his suite, needless to say, it was a much nicer room than Jeff and I had. We went to the bedroom and he opened the curtains. There were floor to ceiling windows that overlooked Lake Shore Drive. It was a spectaculer view to get fucked by, watching all the cars pass by, 10 to 20 stories below, overlooking the lake.