A week ago I (37m) was out of state for a wedding. I was staying at a hotel with my family, who I am still DL with. I was browsing Grindr and Growlr when I got a message. Heavy set, 50-something, bald on top, hairy belly, just my type, asked me if I wanted to hang out in his Jacuzzi. So I snuck away and met this guy. We were at a beach town, he had a small house with a small backyard, but lots of privacy. He was super super shy, which always puts me at ease. I’ll be a little more aggressive but not rip off your clothes aggressive. He said the tub was all prepped and he’d make us some drinks. I’m sitting in this thing nude and he delivers margaritas in swim shorts and gets in. I am now scared I may have gone too fast. He finally notices and laughs and finally takes off his. He tells me he’s never done this before. I kinda don’t believe him. I creep closer and eventually we have decent, fun, clumsy high school hook up. Lots of making out, lots of touching everywhere but the good spots like he was afraid. He jerked me off. It was fine. He kept saying don’t worry about him but I still went down on him. He came so fast. We made out a little more. He jerked me again. Trying to go down on me but didn’t commit. It was cute how nervous he was. Not the most thrilling night but it was fun. Very nostalgic for my first time.
