My first experience was with a much older guy named Richard. He was a senior counselor at a camp where I worked summers while in college.
During my second summer working at the camp, Richard and I ended up having to share a cabin. I had met him the year prior, but because I was just a rookie that year, we had minimal contact. Now, in my second summer, I was familiar with the operation, and, because there were so many kids enrolled, the counselors had to double-up with respect to sleeping accommodations.
One evening early in the season, after the kids had gone to bed for the night, Richard pulled out a large bottle of Jack Daniels. We started playing 5-card stud, taking shots and talking. After about three drinks into the game, he somehow steered the conversation to sex. I didn't have much experience at that point; however, I managed to describe in great detail about the first and only blow-job I had received. He obviously knew I was lying. But that opened the door for him to tell me how much he enjoyed oral sex and how good it felt to have his cock sucked. But, he said his wife didn't like to do it, so she never gave him blowjobs.
Being a lightweight, I was already pretty drunk by that time, so I made a bet with him that if I won the next hand, I would get a day off - with pay - and the use of his truck so I could go into town. He jokingly said ok, BUT, if I lost, I'd have to suck his dick. I never would have imagined that he was serious, so I took the bet.
The next hand, I drew two 10s. Feeling a little cocky, I asked him if he wanted to raise the bet to two days. He reluctantly accepted, adding that if I lost, he would have my ass too. Again, I didn't think he meant it.
It turned out I was wrong.
After the pass cards were dealt, I was stuck with my pair, while he laid down three deuces.