My roommate moved in when he was just 19 years old many years ago. He would spend hours in his room with music playing and I’d see a shadow pulsing coming from under his door so I knew what he was doing. One night I had to sleep on an inflatable mattress in his room because my walls were being painted. He had his hand down his pants while laying on his bed looking at his laptop and I said “It’s fine, just go for it.” He didn’t at first but eventually just pulled it out and went to town on it. I took that as an invitation to do the same.
After that, we just didn’t care anymore and started jacking off in the living room in front of each other all the time. He knew I was gay (he was straight) but he was an exhibitionist and enjoyed showing off so he thought it was hot.
I got a gag gift for him from the Museum of Sex in NYC. It was a black hand towel with gold embroidery on it that says “Cum Rag.” He liked it and we both ended up using it for our sessions.
A year or so later he moved out, got married then eventually moved back into my place with his wife. But not long after he moved in he wanted to get back to jacking off together. So when the wife would be gone for a while I’d get a text from him while he was in the bathroom that said “Got the rag?” Sure enough a few minutes later he would walk into my bedroom butt naked with a huge hard on, lay on my bed and start stroking. We did this many times over the next couple of years until they both went into the Navy.
I snuck plenty of photos and a few videos of him doing his thing, but he’d also randomly send dick pics to me and a few times had me record him cumming. He loved making me hot watching him instead of porn then made sure I got a good view shooting his load.
