My best friend and I had been fooling around for years - since we were 6 or 7. But in High School we really went all out. We vacationed together a lot, and one vacation we shared a hotel room. Before we left for vacation, we played a round of tennis, with the loser the slave for the duration of the vacation. He beat me 6-6 , 6-4. His rules were very simple. Whenever we were in the hotel room, and away from our parents, I had to get naked. I had to suck him whenever he said, and always each night at bed time and each morning to take care of morning wood.
Lastly, I had to masturbate whenever he told me to. Well, the first three days we were pretty busy, and we didn't get back to the hotel 'till like 11 or 11:30. We turned on cable, I got naked, sucked him, masturbated for him and slept. I woke up, sucked him, jerked off and we went out again for the day with our families. Well the fourth day got rainy and our families didn't want to go do the beach/sun stuff, so they decided that our little brothers would like the local children's museum. My friend and I, and his older sister decided we would walk across the street later to catch a movie.
He and I had about 6 hours to kill - so I started sucking. I had already blown him first thing before his shower, and after the last few days my jaws were getting tired. He came, and made me jerk off again. I came a little and as I shot my last spurt he shoved his soft dick in my mouth. I started in again, and I took forever to get it hard.
Eventually he got hard again, I sucked painfully and swallowed more cum. He once again made me jerk off - although he helped me by sucking me for awhile. I came, and once again I was on my knees slurping his dick. Even though my cock was becoming sore and drained, I was developing a real desire to swallow another load. Just the taste of his cum was awesome and I was starting to really think about his cum. I had sucked him off before, maybe 100 times...but never so many times in a row, and swallowing so much.
An hour later, he gets dressed and tells me to stay nude - he's going for cokes. He comes back with his sister who is pretty cute. I run for the covers and he tackles me. He tells me I have a choice of what I do. She asked what that meant and why was I naked. Her told her that she would enjoy this. I decided to jerk off instead of blow him in front of her...but my cock was really sore. It was basically no use, I was in too much pain; I blew him again. She just sat there staring - wide eyed and half smiling. It took a very long time, I sucked like a champ - he blew and I swallowed. she didn't do anything sexy or anything. She just said, 'when you guys are ready come get me for the movie'