After his solo shoot, Thad went home and told his roommates about it who all gave him a big thumbs up. It wasn't too long after that he got in touch asking what he could do next. Of course, I told him he could come back for a happy-ending massage. It took a couple days for him to reply, but the answer was obviously yes!
Thad had only gotten sensual massages during foreplay; he'd gotten the "happy" part, just not the "ending." Being a guy who has been checking things off his bucket list, he said he was pretty excited about trying it. All those massages were from girls, too, so this shoot was checking another one off the list: getting off with the help of a guy for the first time.
Rubbing down his back, I made a few passes between Thad's ass cheeks and, immediately recognized the green light to rub his hole. Thad's thick cock was growing thicker by the minute after I dripped massage oil down his crack and slid my fingers across his magic button.
On his back, Thad must have been deep in some fantasy. I'd love to have known what he was thinking about, but whatever it was was working. I took a little extra time edging him and playing with his fat dick.
Thad hadn't jerked off for 3-4 days before coming over so he was ready to bust. I had taken note of his jerk off style, slowly stroking his cock downward, working the head. Once I started doing the same the game was over. Thad quietly said he was getting close and jizz erupted from his dick.
