Myself and some close business partners hosted an event on the rim of downtown several years ago. A total of maybe 75 guests, loud music, patio, and an open bar. Late night, perhaps midnight, I convinced my then girlfriend to climb up the buildings latter (only 3 flights) to see the roof top view. People who knew about the latter/rooftop were making there way up there randomly throughout the evening, but we were up there alone once we climbed up. We remained up there a good 10 minutes admiring the view and looking down at our guests.
We flirted around and kissed for a bit before I decided to move my hand up her dress and pull her thong off and placed it in my pocket. I then bent her over one of the buildings ac units facing the latter and plowed into her from behind for several minutes. Under the night sky and in the area of downtown and with so many people below the roof downtown was amazing. We stopped and I pulled her over to the rooftops ledge where I then sat with my arms at each side to hold my balance as she started sucking me off while squatting down-it was a roof top, so her knees would have been destroyed. I could tell she was nervous at being caught up there, so I assured her I was keeping an eye on the latter area for anyone who may climb up.
A few minutes later, my blurred vision noticed the top of a guys head at the top of the latter, just high enough to see over the ledge watching us. I had no idea who it was. I immediately asked her to stop and she quickly said “why?!” I asked her to stand up and bend straight over to suck me because I was close to finish. She continued and I made sure to reach back and pull up her dress to expose her ass out to whoever it was watching.
A few minutes later I finished and our mystery guest then vanished from view.
We made our way back down and left within a few minutes. I never found out who was watching but I have got her to do a lot of risky/fun things without her having a care in the world, and sometimes, without her knowing
