Race Day

[Guest FinalDL2021]

This is my story about my first time bareback, I had always been a condom Nazi prior to this experience.

 

There is a Race in San Francisco called Bay to Breakers. You can race, and  its also sort of like Mardi Gras and a 12k Rolled into one; runners get into costumes, some are even erotic, male and female runners are even totally nude. I was not sure if I wanted to mess around or run competitive, I was in great shape that year. I decided what I would do is find some old shorts, and jerry-rig them to be ripped off, by cutting down the side and adding some Velcro to keep them fastened. I also bought a flashy bright red jockstrap online. My plan was, if I was off my time goal, or I developed a cramp, I would drop the shorts and have some fun. I was doing good for the first two miles, then developed a mild cramp in my side, I would give it another mile to go away, it didn't and I started slowing down. I figured it was time to lose the shorts.  So now I was running it a racing T, and a red jockstrap. I was getting a lot of whistles and cat calls, I only hoped I would not run into anyone I knew.

At the finish line, I sort of stayed amongst large crowds, to hide my exposure. the excitement and the euphoria was wearing off fast, I just wanted that personal effects truck to arrive with my sweats so I could get dressed. I felt a tap on my shoulder, and my heart sunk, it was probably someone from my run club. I turned around and met a rather nice looking guy about my age. He said I looked good out there, and not just because of my jockstrap. He said he was a competitive runner as well, the conversation took my mind off my awkwardness. Eventually the truck arrived with my sweats. The man introduced himself as Mike, and wanted to know if I would like to go back to the Wharf and have lunch with him. He said he was also going to meet a few of his friends at a cafe , I sure why not, I said. For some reason, in the back of my mind, I kind of felt he was coming onto me, but I would wait for a sure signal of some sort. 

While at the café, I realized no one else was showing up. I had already ordered and there was no real turning back. I ordered a wine, to help with the bizarre feelings I was having, anxious but becoming aroused at the same time. After my first glass of wine, and I ordered a second, he put his hand on my thigh. I asked him how did he know I would respond the way that I did. He told me it was the red Jockstrap, and that he was also sort of taking a chance. At that time I told him I was straight, yet didn't not mind playing around with men on occasion. I said I had been with 6 other men sexually, since my early 20's. He was cool with that, and said that he was gay. I felt comfortable with him and we wen back to his place. He had an awesome apartment in a part of the City known as Mission Delores, very nice. I was rock hard and pre-cumming by this time, and my heart was pounding. We sat on his couch, he turned on some easy listening music, and conversed and had some more wine.  we started making out, on the couch where we stripped down naked, then went to the shower where we showered and made out for awhile there. We then went to his room where he got out some poppers. I got poppered up, and ready for whatever would happen next.  we did 69 for awhile.  he then said for me to lye on my stomach where he proceeded to rim me out, fantastic. this was the best experience I had with another guy so far. One thing I did observe, was no condoms where ever mentioned. I had to make a quick decision. do I stop everything, and become Mr. condom Nazi, possibly ruining the whole experience. or do I role with it and take my chances. I had to logic it out really fast; Mike was the hottest guy I had been with, he looked very healthy, and he had an awesome place, would I ever get this kind of experience again? for the first time in 17 years, I rolled the dice. It was so natural and awesome feeling him explode into my ass, He was jerking me off, and we almost came together. I was spent and exhausted, I must have slept at his place for several hours. when I woke up, I was panicked, I got dressed said good bye, then went home in a cab. I was freaked for a couple of weeks after. I stayed in touch with Mike, and he said his boyfriend was back in town, and that I was a fun time in the sack. they had an open relationship. He told me he was HIV- and not to worry. I still got tested, every couple of weeks later. two years later I got married, and moved out to the East Coast.

[Guest iJoey]

hot story

[Guest Boxir55]

Nice story. When things are working out well like that I would give in to it as well, its too difficult not to go along with it. 

[Guest iJoey]

Are you still married?

[Guest FinalDL2021]

On ‎6‎/‎12‎/‎2018 at 9:56 AM, ijimmi69 said:

Are you still married?

yes, but its a very tenuous marriage, for reasons other than my sexual identity. If I find myself divorced, I am just diving into a gay lifestyle without holding back.