This is a story about making a NEW FRIEND. Back in the day when Craigslist was thriving I posted an ad looking for a Pump Buddy. This was during the day before heading to work. When home I checked out my replies. There were about a dozen but only 2 were from men whom seemed actually interested in vacuum pumping. I had arrainged to meet with each of them seprately. But only one actually panned out. His name ironiclly was Craig from CL. A mid 20's college student who lived locally. He had his own pumping equipment but had never done a session with anyone before. He was curious what that would be like. But he was hesitant because he did not want his girlfriend to find out he pumped or with whom. We traded emails a few days before he invited me to meet with him. He wanted discretion and total privacy so he asked me to join him sailing on his family's boat.
It was a sunny Sunday afternoon. I wore a swim trunks and a long t shirt. Put on some sunblock I put my vacuum equipment in my gym bag. Stopped on the way picking up snacks and drinks. Drove across town to the marina. Craig met meet at the dock. He wore flip flops a pair of shorts one gold chain around his neck and mirrored sunglasses. The plan was sail out on to Lake Erie. Anchor. Have a few drinks and get some sun. Then go below deck. We chatted a while and got to know each other. We talked about our size and history penis pumping. I had several years more practice then Craig did. But from his description his cock filled more of the tube then mine did. I was eager to get started and felt we were sufficiently alone. I would have been happy to slide on my pump right there on the bench I was seated on. But Craig was nervous someone with binoculars might see us. So he led me below deck. This was a really nice ship. Down the steps we had a small bathroom and shower a pantry area and to the left a bed Craig had made up. With pillows towels and gelled lubricant. In private Craig opened up a bit more. He quickly stripped off his shorts and sat down bare ass naked and invited me to do the same. Boy did this guy have a dark sun tan. He said he wanted to see what my cock and balls looked like unpumped. I dropped my clothes in a pile on the floor and fluffed up my package with a few strokes of my hand. This was our first looks at each other because this was prior to smart phones and digital pictures.