Update, i finally got him alone for the first time in since the last update. He spent Halloween at my place and we started playing with each others dicks over the pants again like last time. This time i told him i wanted to show him my dick and he let me pull it out. He jacked me off and wanted me to slap his face and lips with it. He licked the tip a little before getting overwhelmed and wanted to slow things down. I started jacking him off over his shorts. They were loose so i had a good grip on it. I told him i wanted to put my mouth on it and he let me put it in over the shorts. The shorts were loose enough i got a good mouthful of his cock but he wasnt ready to whip it out still. He has a big thick uncut cock and even through the shorts it felt amazing in my mouth. I started sucking on his nipple while jacking him off over the shorts and he said he was gonna cum. I told him i wanted him to cum and it was okay. I kept going and he moaned a loy, one of the best sounds ive ever heard. He said he was cumming so i put my mouth back on it over the shorts. He grabbed my head and shoved his throbbing big dick in my mouth shorts and all while he busted a huge load. He went crazy while he was cumming. It sounds crazy to do that much and not just go for a full blowjob but i think he just needed something like this in the middle to ease into it. I told him i woulda loved it if he pulled his cock out and let me swallow that load and he said he thought about it and that its most likely gonna happen next time and he wants to make me cum too. He said he loved tasting my cock and he took his time playing with it and just staring at it. It was his first time touching a dick other than his own and he was loving it. No matter what happens next this night will always be one of my best and horniest memories. Will update again next time I see him, am confident it will just keep getting better.