The Challenge - Sex Stories

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The Challenge

Date: 2/25/2015, Categories: First Time, Gay Male, Group Sex, Author: xtremdom, Rating: 100, Source: xHamster

I was sitting around the other day talking with some friends. Our conversation revolved around the theory of how women could pick up anyone they want with little to no effort but men had to work and play games and do all this silly shit even to get a shot at getting laid. Even gay guys! We had to deal with all the drama even from other guys. All the guys laughed and sort of agreed casually. The conversation came to a close and one of our friends who had been listening got in the conversation. SHE said we were all full of it and if we were up to a little bet, she would be interested to see what the outcome would be. The conditions were it was all or nothing. We all had to participate for a specified period and then report back 1 time a week to update each other or no bet. So we agreed. Eric asked what happened if we won the bet. Ashley agreed if we won the bet we all had a free night with her, together or individually or however we wanted it. After a brief discussion we agreed. So, Ashley began with her rules of engagement as we referred to them after that day. Our assignment was for the next week everywhere we went, work, bars, shopping, or anywhere if we had a chance to have a sexual encounter with anyone whether we initiated it or we were approached we must engage. If we didn't we had to be honest and we were out of the equation. However, if we did we had to report back at our weekly meeting of our encounter and brief the others. Sounded simple enough. We were all in ... agreement and it was getting late so we all got ready to head home for the evening. Tim and I made a quick run to the restroom to take a leak before heading out. We walked up to the urinals and did our thing while we talked about what was to come. I hadn't noticed the guy that came in behind us and was at the urinal beside me. Tim and I were still talking when I heard "I could really work over two hot cocks like that". I slowly turned and looked at this guy probably about 25 years old who was holding his cock in his hand and staring at my cock. He was young, clean cut, dark tanned, and looked like a business guy from the suit he was wearing. Tim and I looked at each other in amazement as we were stunned. I had never had anything like this happen and was pretty sure Tim hadn't either. Not that he had ever told me anyway. Tim looked at me and to my surprise said "I guess we have to keep up our end of the deal". He smiled and I turned back to our "new friend". Not really knowing how something like this happened, I slowly said, "ok, so how does this work?" He tucked his cock back and in his pants and zipped up. He loosened his tie and took his jacket off. He stepped over to one of the bathroom stalls and pushed the door opened and paused like he wanted Tim and I to go in. Not really knowing what was happening but running with the moment I stepped into the stall and Tim followed. Our friend stepped in, closed the stall door and locked it. Tim started to speak, when we both were pushed ...